(S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid
• CAS No.: 138423-86-6
• Molecular Formula: C₁₃H₂₃NO₄
• Molecular Weight: 257.33
• Mol file: 138423-86-6.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 4,4-dimethyl-, 1-(1,1-dimethylethyl) 2-methyl ester, (S)-;(S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid;

Chemical Property of (S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.12E-05mmHg at 25°C
• Refractive Index: 1.483
• Boiling Point: 345.1 °C at 760 mmHg
• PKA: -3.26±0.60(Predicted)
• Flash Point: 162.5 °C
• PSA: 66.84000
• Density: 1.117g/cm³
• LogP: 2.04450
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

(S)-1-Boc-4,4-dimethyl-pyrrolidine-2-carboxylicacidmethylester 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid

There total 8 articles about (S)-1-(tert-Butoxycarbonyl)-4,4-dimethylpyrrolidine-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: 94.41%

(S)-5-Hydroxy-4,4-dimethyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester → Methyl (2S)-1-(tert-bytoxycarbonyl)-4,4-dimethylprolinate (138423-86-6)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; at -70 ℃; for 2.5h; Inert atmosphere;

Reference yield: 65.0%

4,4-dimethyl-pyrrolidine-2-carboxylic acid methyl ester + di-tert-butyl dicarbonate (24424-99-5) → Methyl (2S)-1-(tert-bytoxycarbonyl)-4,4-dimethylprolinate (138423-86-6)

Guidance literature:

4,4-dimethyl-pyrrolidine-2-carboxylic acid methyl ester; With dmap; In acetonitrile; at 0 ℃; for 0.166667h; Inert atmosphere; Sealed tube;

di-tert-butyl dicarbonate; In acetonitrile; at 0 - 20 ℃; for 2.5h; Inert atmosphere; Sealed tube;

Reference yield:

O1-tert-butyl O2-methyl (2S)-4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate (158392-74-6) → Methyl (2S)-1-(tert-bytoxycarbonyl)-4,4-dimethylprolinate (138423-86-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃LiBH / tetrahydrofuran / 0.5 h / -78 °C

2: Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 2 h / -78 °C

With triethylsilane; boron trifluoride diethyl etherate; lithium triethylborohydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00094a057

upstream raw materials:

(R)-2-[tert-Butoxycarbonyl-(2-methyl-allyl)-amino]-3-phenylselanyl-propionic acid methyl ester

O₁-tert-butyl O₂-methyl (2S)-4,4-dimethyl-5-oxopyrrolidine-1,2-dicarboxylate

(S)-3-(tert-butoxycarbonylamino)-oxetan-2-one

(2-Methyl-allyl)-((S)-2-oxo-oxetan-3-yl)-carbamic acid tert-butyl ester

Downstream raw materials:

(S)-4,4-Dimethyl-pyrrolidine-2-carboxylic acid methyl ester; hydrochloride

(2S)-1-(tert-butoxycarbonyl)-4,4-dimethylpyrrolidine-2-carboxylic acid

C₂₀H₂₆BrNO₅

C₂₀H₂₆BrN₃O₂

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