(S)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 1314325-24-0
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Mol file: 1314325-24-0.mol

Synonyms:(S)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of (S)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (S)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester

There total 2 articles about (S)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-methoxycarbonylphenyl bromide (619-42-1) + tert-butyl pyrrolidine-1-carboxylate (86953-79-9) → (R)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester (885044-25-7) + (S)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester (1314325-24-0)

Guidance literature:

tert-butyl pyrrolidine-1-carboxylate; With C₁₃H₂₆N₂; sec.-butyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; In tert-butyl methyl ether; cyclohexane; at -78 - -74 ℃; for 3h; Inert atmosphere;

With zinc(II) chloride; In diethyl ether; tert-butyl methyl ether; cyclohexane; at -74 - 20 ℃; Inert atmosphere;

4-methoxycarbonylphenyl bromide; With palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; In diethyl ether; tert-butyl methyl ether; cyclohexane; at 20 ℃; for 16h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/jo2011347

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) + methyl 4-iodobenzoate (619-44-3) → (R)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester (885044-25-7) + (S)-2-(4-methoxycarbonylphenyl)pyrrolidine-1-carboxylic acid tert-butyl ester (1314325-24-0)

Guidance literature:

With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); 3,6-bis(dimethylamino)-9-mesityl-10-methylacridinium bromide salt; caesium carbonate; In N,N-dimethyl-formamide; at 30 ℃; for 3h; Reagent/catalyst; Overall yield = 86 %; Overall yield = 26.2 mg; Optical yield = 4 %ee; Inert atmosphere; Irradiation;

DOI:10.1002/anie.201711296

upstream raw materials:

4-methoxycarbonylphenyl bromide

tert-butyl pyrrolidine-1-carboxylate

1-(tert-butoxycarbonyl)-L-proline

methyl 4-iodobenzoate