Category: 141449-85-6

Synthetic Route of 141449-85-6, 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. 141449-85-6 name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, 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 mixture of 29 (0.123 g; 0.27 mmol), 139 (0.063 g, 0.30 mmol), NaI (0.040g ; 0.27 mmol) and K2CO3 (0.045 g; 0.32 mmol) in dimethylacetamide (3 ml) was heated at [85C] under argon atmosphere for 3 hours. The crude mixture was evaporated and purified by flash chromatography eluting with a gradient [1-3%] of 3.5 N [NH3 IN MEOH/METHYLENE] chloride to give after trituration in ether/pentane Example 51 as a white solid. Yield: [78%] MS-ESI: 631 [[M+H] +] [1H NMR (CDC13)] : 1.31 (m, 6H); 1.45 (s, 9H); 1.50-1. 75 (m, 4H); 1.62 (s, 6H); 2.35 (s, 6H); 2.72 (m, 2H); 2.80 (m, 4H); 2.94 (m, 2H); 3.25 (br m, 2H); 3.55 (br m, 2H); 4.10-4. 20 (br m, 1H); 4.70-4. 80 (br m, 1H); 6.74 (s, 1H) ; 6.95 (s, 1H); 7.07 (s, 2H); 8.12 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2004/18480; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthetic Route of 141449-85-6, 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. 141449-85-6 name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, 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 40-mL vial was charged with 4-chlorobenzaldehyde (1.13 g, 8.04 mmol, 1.00 equiv), 1,2-dichloroethane (20 mL), tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(lH)-carboxylate (1.69 g, 7.96 mmol, 0.99 equiv) and sodium triacetoxyborohydride (5.09 g, 24.0 mmol, 2.99 equiv). The resulting solution was stirred overnight at room temperature and quenched by water (10 mL). The mixture was extracted with DCM (3 x 30 mL) and the organic layers were combined, washed with water (3 x 10 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was chromatographed on a silica gel column to provide 2.15 g (79% yield) of tert-butyl 5-(4-chlorobenzyl)hexahydropyrrolo[3,4-c]pyrrole-2(lH)- carboxylate as an off-white solid. LCMS (ESI, m/z): 337 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; JONES, Todd K.; DUNCAN, Katharine K.; WEBER, Olivia D.; CISAR, Justin S.; MERIT, Jeffrey E.; (184 pag.)WO2017/87858; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 141449-85-6 as follows. category: amides-buliding-blocks

A flask was charged with tert-butyl octahydropyrrolo[3,4-c]pyrrole-2-carboxylate (1.20 g, 5.65 mmol, 1.00 equiv), potassium (bromomethyl)trifluoroboranuide (1.13 g, 5.63 mmol, 1.00 equiv), and THF (15 mL) under nitrogen. The mixture was stirred overnight at 80 C and concentrated under reduced pressure. Potassium carbonate (0.781 g, 5.65 mmol, 1.00 equiv) and acetone (10 mL) were added. The resulting solution was stirred for 2 h at room temperature, dissolved in acetone (2 x 200 mL) and filtered. The filtrate was concentrated under reduced pressure to provide 1.40 g (75% yield) of potassium ((5-(tert- butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(lH)-yl)methyl)trifluoroborate as a yellow solid. LCMS (ESI, m/z): 293 [M-K]”.

According to the analysis of related databases, 141449-85-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABIDE THERAPEUTICS, INC.; GRICE, Cheryl A.; WIENER, John J. M.; WEBER, Olivia D.; DUNCAN, Katharine K.; (364 pag.)WO2018/217805; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A common heterocyclic compound, 141449-85-6, name is tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate, molecular formula is C11H20N2O2, 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. 141449-85-6.

The 5 – chloro – 1, 6 – naphthyridine (0.93 g, 5 . 65 mmol), hexahydro-pyrrolo [3, 4 – c] pyrrole -2 (1 H) – formic acid tert-butyl ester (1.00 g, 4 . 71 mmol), three (dibenzylidene acetone) two palladium (0.43 g, 0 . 47 mmol), 2 – dicyclohexyl phosphorus – 2, 4, 6 – triisopropyl biphenyl (0.46 g, 0 . 94 mmol), sodium tertiary butyl alcohol (1.40 g, 14.1 mmol) and toluene (20 ml) are added to the 100 ml single-port in the bottle, under the protection of nitrogen, reaction temperature to 120 C reaction 36 hours. Stopping the reaction, the reaction solution is distilled under reduced pressure to remove the solvent after purification by silica gel column chromatography (petroleum ether/ethyl acetate (v/v)=1/1) to obtain the title compound (light yellow liquid, 1.15 g, 71.7%).

The synthetic route of tert-Butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Lao Jinhua; Nie Biao; Xu Juan; (35 pag.)CN107759620; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics