(S)-tert-Butyl 4,4-difluoro-2-(hydroxymethyl)-pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (S)-tert-Butyl 4,4-difluoro-2-(hydroxymethyl)-pyrrolidine-1-carboxylate
• CAS No.: 215918-21-1
• Molecular Formula: C10H17F2NO3
• Molecular Weight: 237.247
• Hs Code.: 2933990090
• Mol file: 215918-21-1.mol

Synonyms:(S)-tert-Butyl 4,4-difluoro-2-(hydroxymethyl)-pyrrolidine-1-carboxylate;(S)-1-Boc-2-(hydroxyMethyl)-4,4-difluoropyrrolidine;tert-butyl (2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Chemical Property of (S)-tert-Butyl 4,4-difluoro-2-(hydroxymethyl)-pyrrolidine-1-carboxylate

Chemical Property:

• Vapor Pressure: 0.000183mmHg at 25°C
• Boiling Point: 293.4°C at 760 mmHg
• PKA: 14.77±0.10(Predicted)
• Flash Point: 131.3°C
• PSA: 49.77000
• Density: 1.21g/cm³
• LogP: 1.56130
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl (2S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylate 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-tert-Butyl 4,4-difluoro-2-(hydroxymethyl)-pyrrolidine-1-carboxylate

There total 8 articles about (S)-tert-Butyl 4,4-difluoro-2-(hydroxymethyl)-pyrrolidine-1-carboxylate 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: 100.0%

1-(tert-butoxycarbonyl)-4,4-difluoro-L-proline (203866-15-3) → (S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (215918-21-1)

Guidance literature:

1-(tert-butoxycarbonyl)-4,4-difluoro-L-proline; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -10 ℃; for 0.75h;

With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 ℃; for 2h;

With ammonium chloride; In tetrahydrofuran; water; at 20 ℃;

Reference yield: 99.0%

1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate (203866-17-5) → (S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (215918-21-1)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 25.25h;

DOI:10.1016/j.ejmech.2013.04.011

Reference yield:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (S)-4,4-difluoro-2-(hydroxymethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (215918-21-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

2: 93 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

3: 90 percent / DAST / CH₂Cl₂ / -78 - 20 °C

4: DIBAL-H / tetrahydrofuran / -78 - 20 °C

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2003.08.075

upstream raw materials:

1-tert-butyl 2-methyl (2S)-4,4-difluoropyrrolidine-1,2-dicarboxylate

1-(tert-butoxycarbonyl)-4,4-difluoro-L-proline

di-tert-butyl dicarbonate

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

methyl 4-[1-(tert-butoxycarbonyl)-4,4-difluoro-(2S)-pyrrolidinyl]methoxybenzoate

C₄₁H₄₆F₄N₆O₄

C₄₅H₅₂F₄N₈O₆

(R)-2-(4,4-difluoro-1-(4-(2-methylbenzyl)phenyl)pyrrolidin-2-yl)acetic acid

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