Category: 239074-29-4

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate

b) ((1r,4r)-4-(tert-Butoxycarbonylamino)cyclohexyl)methyl 4-methylbenzene-sulfonate A solution of 4-methylbenzene-1-sulfonyl chloride (2.28 g, 11.96 mmol) in dichloromethane was added to a solution of tert-butyl (1r,4r)-4-(hydroxymethyl)cyclohexylcarbamate (Preparation 50a, 2.11 g, 9.2 mmol) and triethylamine (1.59 mL, 11.4 mmol) in dichloromethane (50 mL) and the mixture was stirred overnight at room temperature. The mixture was washed with 1 M aqueous sodium hydroxide solution and the organic layer was dried (MgSO4) evaporated and the residue was purified by flash chromatography (diethyl ether/hexanes) to give the title compound (2.91 g, 83%) as a white solid. LRMS (m/z): 382 (M-H)+.1 H NMR (300 MHz, CDCl3) delta ppm 0.90 – 1.12 (m, 4H), 1.43 (s, 3H), 1.78 (dd, 2H), 1.99 (d, 2H), 3.34 (m, 1H), 3.46 (t, 1H), 3.81 (d, 2H), 4.37 (m, 1H), 7.34 (d, 2H), 7.77 (d, 2H).

According to the analysis of related databases, 239074-29-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi; WO2011/157397; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 239074-29-4,Some common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, molecular formula is C12H23NO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A suspension of 4-hydroxy-5 -methyl-6-oxo-5,6-dihydro- 1,5 -naphthyridine-3- carbonitrile (100 mg, 0.50 mmol) in THF (10 mL) was stirred at rt and treated with (1,1- dimethylethyl [tralpha/?5-4-(hydroxymethyl)cyclohexyl] carbamate (114 mg, 0.50 mmol), triphenyl phosphine (261 mg, 0.99 mmol) and DIAD (0.20 mL, 0.99 mmol) added dropwise. The resulting pale yellow suspension was stirred at rt for 20 min then heated at 80 0C overnight. The reaction was then heated at 60 0C over the weekend. The reaction was then evaporated to give a yellow gum which was purified by silica chromatography, eluting with MeOH/DCM (0-10%) to give the title compound (0.51 g), containing residual triphenylphosphine oxide. This may be used in the next step without further purification.MS (ES+) m/z 413 [MH+].

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; JONES, Graham, Elgin; MARKWELL, Roger, Edward; HENNESSY, Alan Joseph; MILES, Timothy; PEARSON, Neil David; WO2010/45987; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 239074-29-4,Some common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, molecular formula is C12H23NO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A suspension of 4-hydroxy-5 -methyl-6-oxo-5,6-dihydro- 1,5 -naphthyridine-3- carbonitrile (100 mg, 0.50 mmol) in THF (10 mL) was stirred at rt and treated with (1,1- dimethylethyl [tralpha/?5-4-(hydroxymethyl)cyclohexyl] carbamate (114 mg, 0.50 mmol), triphenyl phosphine (261 mg, 0.99 mmol) and DIAD (0.20 mL, 0.99 mmol) added dropwise. The resulting pale yellow suspension was stirred at rt for 20 min then heated at 80 0C overnight. The reaction was then heated at 60 0C over the weekend. The reaction was then evaporated to give a yellow gum which was purified by silica chromatography, eluting with MeOH/DCM (0-10%) to give the title compound (0.51 g), containing residual triphenylphosphine oxide. This may be used in the next step without further purification.MS (ES+) m/z 413 [MH+].

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; JONES, Graham, Elgin; MARKWELL, Roger, Edward; HENNESSY, Alan Joseph; MILES, Timothy; PEARSON, Neil David; WO2010/45987; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Related Products of 239074-29-4,Some common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, molecular formula is C12H23NO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Alcohol (79.5 g, 347 mmol) was dissolved in tetrahydrofuran (800 ml). Triethylamine (72.5 ml, 520 mmol) and methanesulfonyl chloride (32.2 ml, 416 mmol) were sequentially added thereto under ice-cooling with stirring and the mixture was reacted for 1.5 hour. The reactant was poured into aqueous citric acid (citric acid monohydrate 30 g in water 500 ml) to become pH 4 and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate anhydrous. The solvent was removed under reduced pressure. The crystal deposited in the removal process was collected by filtration and washed with hexane to give mesylate (100 g). The obtained mesylate was dissolved in dimethylformamide (100 ml) and sodium azide (63.7 g, 980 mmol) was added thereto and reacted at 80 C. for 2 hours. The reactant was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate anhydrous. The solvent was removed under reduced pressure to quantitatively give the desired Azide (the crude weight is 85.4 g).1H-NMR (DMSO-d6) delta ppm: 0.90-1.21 (m, 4H), 1.32-1.50 (m, 1H), 1.37 (s, 9H), 1.65-1.84 (m, 4H), 3.06-3.24 (m, 3H), 6.71 (d, 1H, J=8.1 Hz).

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; US2010/273841; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, belongs to amides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 239074-29-4, SDS of cas: 239074-29-4

To a stirred solution of tert-butyl ((1R,4R)-4-(hydroxymethyl)cyclohexyl)carbamate (1.5 g, 0.7 mmol, synthesized via Steps 1-2 of Intermediate K) and 1-phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate (4.74 g, 0.98 mmol, Intermediate X) in THF (30 mL) was added KOH (3.67 g, 65.4 mmol) at rt. The resulting reaction mixture then heated to 60 C. and stirred for 16 h. The reaction mixture was then transferred into ice water and the resulting mixture was extracted using ethyl acetate (3¡Á100 mL). The combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the crude product was purified using silica gel column chromatography (2% MeOH-DCM) to give tert-butyl ((1R,4R)-4-(18-phenyl-2,5,8,11,14,17-hexaoxaoctadecyl)cyclohexyl)carbamate as a yellow oil (0.92 g, 26%). LC-MS (ESI+) m/z 557.4 (M+18)+.

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Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: amides-buliding-blocks

To a solution of tert-butyl N-[4-(hydroxymethyl)cyclohexyl]carbamate (S9, 0.92 g, 4.00mmol) and N,N-diisopropylethylamine (1.05 mL, 6.00 mmol) in CH2Cl2 (20 mL, 0.2 M) cooledto 0 C was added methanesulfonyl chloride (0.34 mL, 4.40 mmol) dropwise. After 5 min thereaction was warmed to 23 C and stirred for 2 h. A saturated solution of aqueous NaHCO (30mL) was added to quench the reaction. The organic phase was separated and the aqueous phasewas extracted with CH2Cl2 (2 ¡Á 10 mL). The combined organics were dried over MgSO4,filtered, and the filtrate was concentrated under reduced pressure. The crude material was driedunder hi-vac to afford crude [4-(tert-butoxycarbonylamino)cyclohexyl]methyl methanesulfonate(S10, 1.24 g, >99% yield) which was used without further purification.

The synthetic route of 239074-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Allegretti, Paul A.; Horton, Timothy M.; Abdolazimi, Yassan; Moeller, Hannah P.; Yeh, Benjamin; Caffet, Matthew; Michel, Guillermina; Smith, Mark; Annes, Justin P.; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

239074-29-4, The chemical industry reduces the impact on the environment during synthesis 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, I believe this compound will play a more active role in future production and life.

Trans (4-Amino-cyclohexyl)-acetonitrileTrans Methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohexylmethyl esterTrans (4-hydroxymethyl-cyclohexyl)-carbamic acid tert-butyl ester (3.49 g, 15.0 mmol) in DCM (50 mL) was treated with pyridine (4.98 mL, 60.8 mmol). The mixture was cooled to 0 C and methanesulfonyl chloride (2.36 mL, 30.4 mmol) was added dropwise over 5 minutes. The mixture was stirred at room temperature for 5 hours and then concentrated under vacuum. The residue was partitioned between ethyl acetate and water and the aqueous phase extracted with ethyl acetate (x2). The combined organic extracts were washed with brine, dried with sodium sulfate and concentrated under vacuum. The residue was triturated with cyclohexane then dried under vacuum to give a white solid. Further purification by column chromatography on silica gel (eluting with 1 : 1 cyclohexane/ethyl acetate) gave 4.17 g (90%) of trans methanesulfonic acid 4- tert-butoxycarbonylamino-cyclohexylmethyl ester as a white solid. 1H NMR (400 MHz, CDCI3) delta: 4.37 (br s, 1 H), 4.02 (d, 2 H), 3.39 (br s, 1 H), 3.00 (s, 3 H), 2.11-2.00 (m, 2 H), 1.91-1.81 (m, 2 H), 1.77-1.64 (m, 1 H), 1.43 (s, 9 H), 1.18-1.05 (m, 4 H).

The chemical industry reduces the impact on the environment during synthesis tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HURLEY, Christopher; KULAGOWSKI, Janusz; ZAK, Mark; WO2013/7768; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

239074-29-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 239074-29-4 as follows.

To a solution of tert-butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate (0.84 g, 3.65 mmol) in THF (15 mL) was added No.23 triphenylphosphine (1.43 g, 5.45 mmol) and No.23 4,6-dichloropyrimidin-5-ol (0.68 g, 3.65 mmol). To the mixture was added No.23 diisopropylazodicarboxylate (1.47 g, 7.27 mmol) at 0C., the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=40:1 as eluent) to afford the tert-butyl (trans-4-(((4,6-dichloropyrimidin-5-yl)oxy)methyl)cyclohexyl)carbamate as colorless oil (0.45 g, 33% yield). LC/MS APCI: Calculated 375.11; Observed m/z [M-99 (boc)]+ 276.1. 1H-NMR 400 MHz, DMSO-d6: delta 8.68 (s, 1H), 6.75 (d, J=7.60 Hz, 1H), 3.94 (d, J=6.00 Hz, 2H), 3.16-3.14 (m, 1H), 1.89-1.79 (m, 4H), 1.73-1.71 (m, 1H), 1.38 (s, 9H), 1.19-1.16 (m, 4H).

According to the analysis of related databases, 239074-29-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Arrien Pharmaceuticals LLC; Vankayalapati, Hariprasad; US2020/131154; (2020); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 239074-29-4

To a mixture of 7-fluoro-8-hydroxy-l-methyl-2(lH)-quinoxalinone (150 mg), 1,1- dimethylethyl [tralpha/?5-4-(hydroxymethyl)cyclohexyl] carbamate (142 mg, 0.618 mmol, for a preparation see Example l(g)) and triphenylphosphine (195 mg, 0.742 mmol) in THF (10 mL) was added DIAD (0.144 mL, 0.742 mmol) and the mixture was stirred at rt for 1 h then triphenylphosphine (195 mg, 0.742 mmol) and DIAD (0.144 mL, 0.742 mmol) were added and the reaction was stirred at rt overnight. The solvent was evaporated and the residue was purified using silica chromatography (0-20%CH3CN/DCM) to afford the title compound (272 mg) which was used in the next step without further purification. MS (ES+) m/z 423 [MNH4+].

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 239074-29-4.

Reference:
Patent; GLAXO GROUP LIMITED; JONES, Graham, Elgin; MARKWELL, Roger, Edward; HENNESSY, Alan Joseph; MILES, Timothy; PEARSON, Neil David; WO2010/45987; (2010); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

239074-29-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 239074-29-4, name is tert-Butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate, A new synthetic method of this compound is introduced below.

b) ((1r,4r)-4-(Tert-Butoxycarbonylamino)cyclohexyl)methyl 4-methylbenzene-sulfonate A solution of 4-methylbenzene-1-sulfonyl chloride (2.28 g, 11.96 mmol) in dichloromethane was added to a solution of tert-butyl (1r,4r)-4-(hydroxymethyl) cyclohexylcarbamate (Preparation 14a, 2.11 g, 9.2 mmol) and triethylamine (1.59 mL, 11.4 mmol) in dichloromethane (50 mL) and the resulting mixture was stirred overnight at ambient temperature. The mixture was washed with 1M aqueous sodium hydroxide solution and the organic layer was dried (MgSO4), evaporated and the residue was purified by flash chromatography (diethyl ether/hexanes) to give the title compound (2.91 g, 83%) as a white solid. LRMS (m/z): 382 (M-H)+. 1H NMR delta (300 MHz, CDCl3): 0.90-1.12 (m, 4H), 1.43 (s, 3H), 1.78 (dd, 2H), 1.99 (d, 2H), 3.34 (m, 1H), 3.46 (t, 1H), 3.81 (d, 2H), 4.37 (m, 1H), 7.34 (d, 2H), 7.77 (d, 2H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Almirall, S.A.; EP2527344; (2012); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics