Category: 111300-06-2

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. 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, A new synthetic method of this compound is introduced below., Formula: C11H21NO3

To a solution of tert-butyl N-(4- hydroxycyclohexyl)carbamate (710 mg, 3.30 mmol, 1.10 equiv) in 10 mL of distilled THF was added sodium hydride (60% dispersion in mineral oil, 720 mg, 18.00 mmol, 6.00 equiv) at room temperature under nitrogen. After stirring for 30 min, intermediate 15.4 (891 mg, 3.00 mmol, 1.00 equiv) in THF (10 mL) was added via syringe and the resulting solution was stirred for 12 h at room temperature. The reaction was then quenched by the addition of water and extracted with 3 x 50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was loaded onto a silica gel column with ethyl acetate/petroleum ether (1 :4 to 1 :2). Purification afforded 18.1 (260 mg, 18%) as a white solid.

The synthetic route of 111300-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS IRIS, INC.; HARRIMAN, Geraldine, C.; WESTER, Ronald T.; ROMERO, Donna L.; ROBINSON, Shaughnessy; SHELLEY, Mee; WESSEL, Matthew David; GREENWOOD, Jeremy Robert; MASSE, Craig E.; KAPELLER-LIBERMANN, Rosana; WO2013/106535; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 111300-06-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 111300-06-2 name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of tert-butyl N-(4- hydroxycyclohexyl)carbamate (412 mg, 1.91 mmol, 1.10 equiv) in freshly distilled tetrahydrofuran (10 mL) was treated with sodium hydride (60% dispersion in mineral oil, 280 mg, 4.00 equiv) for 1 h at room temperature under nitrogen. To this mixture was then added a solution of 16.3 (510 mg, 1.72 mmol, 1.00 equiv) in dry tetrahydrofuran (5 mL) via syringe. After stirring overnight at room temperature, the reaction was then quenched with water and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine and dried over sodium sulfate. After filtration and concentration under reduced pressure, the residue was loaded onto a silica gel column with ethyl acetate/petroleum ether (1:2) and purified to afford ethyl 2-[(35)-12-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-7-thia-9,l l- diazatricyclo[6.4.0.0A[2,6]]dodeca-l(12),2(6),8,10-tetraen-3-yl]acetate (16.4, 400 mg, 49%) as a yellow oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; NIMBUS IRIS, INC.; HARRIMAN, Geraldine, C.; WESTER, Ronald T.; ROMERO, Donna L.; ROBINSON, Shaughnessy; SHELLEY, Mee; WESSEL, Matthew David; GREENWOOD, Jeremy Robert; MASSE, Craig E.; KAPELLER-LIBERMANN, Rosana; WO2013/106535; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, A new synthetic method of this compound is introduced below., category: amides-buliding-blocks

Compound 2 (15 g, 57.47 mmol),trans-4-BOC-aminocyclohexanol (24.7g, 114.9mmol),Triphenylphosphine (30.1 g, 114.9 mmol) and 150 ml of THF were cooled to 0 C in an ice-salt bath.Add DIAD (23.2g, 114.9mmol) dropwise,Warm to room temperature and stir overnight.Column chromatography gave 13.1 g of solid, yield: 49.7%.

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; Shanghai Pharmaceutical Industry Institute; China Pharmaceutical Industry Zongyuan; Zheng Nan; Hao Qun; Zhou Weicheng; Lin Kuaile; Pan Jing; Chen Liang; Zhou Ting; Liu Zhenren; (39 pag.)CN110655519; (2020); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 111300-06-2,Some common heterocyclic compound, 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, molecular formula is C11H21NO3, 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 solution of frans-N-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}- formamide in anhydrous THF at 0C may be treated with borane-THF complex in THF (1 M, excess). The reaction may be allowed to come to room temperature and may be monitored by LCMS until the reaction is complete. The reaction may be quenched with MeOH and the solvents may be removed under reduced pressure. The crude product may be purified by flash chromatography using with 1 – 5 % (2N N H3 in MeOH) in DCM to give frans-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]- cyclohexyl}-methyl-amine. The neutral amine may be treated with 2N HCI in diethyl ether and DCM.The volatiles may be removed under reduced pressure and the salt may be triturated with diethyl ether and filtered to provide the title compound. LCMS: m/z 439 [M + 1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, its application will become more common.

Reference:
Patent; TRANSTECH PHARMA, INC.; GOHIMUKKULA, Devi, Reddy; JONES, David; QABAJA, Ghassan; ZHU, Jeff, Jiqun; COOPER, Jeremy, T.; BANNER, William, Kenneth; SUNDERMANN, Kurt; BONDLELA, Muralidhar; RAO, Mohan; WANG, Pingzhen; GOWDA, Raju, Bore; ANDREWS, Robert, C.; GUPTA, Suparna; HARI, Anitha; WO2011/103091; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)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. Safety of tert-Butyl (trans-4-hydroxycyclohexyl)carbamate

(1) To a solution of tert-butyl(trans-4-hydroxycyclohexyl)carbamate (1.08 g, 5.00 mmol) and 15-crown 5 (1.04 mL, 5.25 mmol) in tetrahydrofuran was added sodium hydride (60% dispersion in mineral oil, 440 mg, 11.0 mmol) at 0 C., followed by iodomethane (0.327 mL, 5.25 mmol) at 0 C. After being stirred for 2 hour, the reaction mixture was poured into water. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, died over sodium sulfate, filtrated and concentrated in vacuo. The residue was purified by silica gel column chromatography to give tert-butyl(trans-4-methoxycyclohexyl)carbamate as a colorless solid (796 mg, 69%). MS (APCI): m/z 247 (M+NH4), 230 (M+H).

The synthetic route of 111300-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kawanishi, Eiji; Matsumura, Takehiko; US2011/160206; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 111300-06-2, 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. 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of PPh3 (1.17 g, 4.47 mmol) in anhydrous toluene (30 mL) was added di-tertbutylazodicarboxylate (DBAD) (1.03 g, 4.47 mmol) at 0 C., and the reaction mixture was stirred for 15 min, after which compound 37-6 (1.40 g, 3.19 mmol) and compound 41-5-1 (894.05 mg, 4.15 mmol) were added and the resulting mixture was stirred at 60 C. for 12 h, the starting materials disappeared. To the mixture, water (100 mL) was added, and the solution was extracted with EtOAc (100 mL¡Á3). The organic phases were combined, dried over anhydrous Na2SO4, and concentrated to give a crude product which was purified by column chromatography (PE/EtOAc=10/1) to afford compound 43-7 (2.00 g, 89.77%) as white solid. LCMS (ESI) m/z: 636 (M+1).

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

Reference:
Patent; Hubei Bio-Pharmaceutical Industrial Technological Institute Inc.; Humanwell Healthcare (Group) Co., Ltd.; Wang, Xuehai; Wu, Chengde; Xu, Yong; Shen, Chunli; Li, Li’e; Hu, Guoping; Yue, Yang; Li, Jian; Guo, Diliang; Shi, Nengyang; Huang, Lu; Chen, Shuhui; Tu, Ronghua; Yang, Zhongwen; Zhang, Xuwen; Xiao, Qiang; Tian, Hua; Yu, Yanping; Chen, Hailiang; Sun, Wenjie; He, Zhenyu; Shen, Jie; Yang, Jing; Tang, Jing; Zhou, Wen; Yu, Jing; Zhang, Yi; Liu, Quan; (251 pag.)US2017/313683; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 111300-06-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)carbamate belongs to amides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of lithium aluminium hydride (9 g, 0.23 mol) in tetrahydrofuran (425 mL) was added slowly tert-butyl (trans-4-hydroxycyclohexyl)carbamate (intermediate 1, 10 g, 0.046 mol). The mixture was refluxed overnight. Once the mixture was cooled to room temperature, 9 ml of water, 9 ml of 4N NaOH solution and 18 ml of water were carefully and successively dropped. The organic solvent was removed under reduced pressure and the crude obtained was dissolved with chloroform and dried over magnesium sulphate. The filtrate was evaporated to dryness and co evaporated with hexane to give the title compound as a white solid (89%). This intermediate is also described in . 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.04 – 1.20 (m, 2 H) 1.25 – 1.40 (m, 2 H) 1.97 (br. s., 4 H) 2.27 – 2.40 (m, 1 H) 3.57 – 3.70 (m, 1 H)

The synthetic route of tert-Butyl (trans-4-hydroxycyclohexyl)carbamate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Almirall, S.A.; Aiguade Bosch, Jose; Gual Roig, Silvia; Prat Quinones, Maria; Puig Duran, Carlos; EP2592077; (2013); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

111300-06-2, name is tert-Butyl (trans-4-hydroxycyclohexyl)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. Recommanded Product: tert-Butyl (trans-4-hydroxycyclohexyl)carbamate

ferf-Butyl (frans-4-methoxycyclohexyl)carbamate: In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of ferf-butyl (frans-4-hydroxycyclohexyl)carbamate (200 mg, 0.93 mmol) in CH2CI2 (4.5 mL) at rt was treated with powdered molecular sieves 3A, 1 ,8- bis(dimethylamino)naphthalin (498 mg, 2.32 mmol) and trimethyloxomium tetrafluoroborate (289 mg, 1.86 mmol). The reaction mixture was stirred at rt for 2 days. The reaction mixture was filtered, the org. phase was washed with 1 N aq. HCI, brine, dried over MgS04, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (7:3 hept-EA) gave the title compound as off-white solid: TLC: rf (7:3 hept-EA) = 0.22

The synthetic route of 111300-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CORMINBOEUF, Olivier; CREN, Sylvaine; LEROY, Xavier; POZZI, Davide; WO2015/19325; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics