(2S,4S)-N-Boc-4-methylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4S)-N-Boc-4-methylpyrrolidine-2-carboxylic acid
• CAS No.: 364750-81-2
• Molecular Formula: C11H19 N O4
• Molecular Weight: 229.276
• Hs Code.: 29339900
• Mol file: 364750-81-2.mol

Synonyms:(2S,4S)-1-(tert-Butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid; (2S,4S)-4-Methyl-1,2-pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester

Chemical Property of (2S,4S)-N-Boc-4-methylpyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.29E-05mmHg at 25°C
• Boiling Point: 343 ºC
• PKA: 4.02±0.40(Predicted)
• Flash Point: 161 ºC
• PSA: 66.84000
• Density: 1.150
• LogP: 1.65440
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,4S)-1-(tert-Butoxycarbonyl)-4-methylpyrrolidine-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,4S)-N-Boc-4-methylpyrrolidine-2-carboxylic acid

There total 7 articles about (2S,4S)-N-Boc-4-methylpyrrolidine-2-carboxylic acid 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: 94.0%

(2S,4S)-tert-butyl 2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate (540501-56-2) → N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline (364750-81-2,871727-77-4)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In phosphate buffer; acetonitrile; at 40 ℃; for 18h;

DOI:10.1021/ja061793d

Reference yield: 60.0%

tert-butylamine (S)-1-(tert-butoxycarbonyl)-4-(methylene)pyrrolidine-2-carboxylic acid (1262320-71-7) → N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline (364750-81-2,871727-77-4)

Guidance literature:

With hydrogen; 5% Pd(II)/C(eggshell); In water; for 8h; under 2250.23 Torr; Industry scale;

Reference yield: 12.0%

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-Butyloxycarbonyl-(2S,4S)-4-methylproline (364750-81-2,871727-77-4) + (2S)-2-(ter-butoxycarbonylamino)-4,4-dimethyl-4-butanolide + (2S,4R)-1-[(tert-butoxy)carbonyl]-4-methylpyrrolidine-2-carboxylic acid (364750-80-1,871727-77-4)

Guidance literature:

Multistep reaction;

DOI:10.1021/ja016280f

upstream raw materials:

L-leucine

di-tert-butyl dicarbonate

(2S,4S)-tert-butyl 2-(hydroxymethyl)-4-methylpyrrolidine-1-carboxylate

N-Boc-4-methylproline methyl ester

Downstream raw materials:

C₁₇H₂₄N₄O₅

C₁₉H₂₄BrN₃O₂

(S)-pyrrolidine-1,2-dicarboxylic acid 2-[2-(4-bromophenyl)-2-oxoethyl]ester 1-tert-butyl ester

{(S)-2-methyl-1-[(2S,4S)-4-methyl-2-(7-{4-[(4-(piperidin-4-yl)piperazine-1-carbonyl)amino]-2-trifluoromethoxyphenyl}-3H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carbonyl]propyl}carbamic acid methyl ester

Refernces

• 1、 -. "HEPATITIS C VIRUS INHIBITORS". Page/Page column 146. . Retrieved 2012/02/15.
• 2、 Gao, Xuguang,Liu, Yuqing,Kwong, Shuqi,Xu, Zhengshuang,Ye, Tao. "Total synthesis and stereochemical reassignment of bisebromoamide". supporting information; experimental part. p. 3018 - 3021. Retrieved 2010/11/16.