Methyl (2R,4S)-1-Boc-4-fluoropyrrolidine-2-carboxylate

Base Information

• Chemical Name: Methyl (2R,4S)-1-Boc-4-fluoropyrrolidine-2-carboxylate
• CAS No.: 647857-39-4
• Molecular Formula: C11H18FNO4
• Molecular Weight: 247.26300
• Mol file: 647857-39-4.mol

Synonyms:40791 (2R,4S)-1-TERT-BUTYL 2-METHYL 4-FLUOROPYRROLIDINE-1,2-DICARBOXYLATE;4S-fluoropyrrolidine-1,2R-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;(2R,4S)-1-tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate;4-(S)-fluoropyrrolidine-N1,2-(R)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;1-tert-butyl 2-methyl (2R,4S)-4-fluoropyrrolidine-1,2-dicarboxylate;

Chemical Property of Methyl (2R,4S)-1-Boc-4-fluoropyrrolidine-2-carboxylate

Chemical Property:

• PSA: 55.84000
• LogP: 1.44480

Purity/Quality:

99%, ^*data from raw suppliers

1-tert-Butyl 2-methyl (2R,4S)-4-fluoropyrrolidine-1,2-dicarboxylate 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl (2R,4S)-1-Boc-4-fluoropyrrolidine-2-carboxylate

There total 6 articles about Methyl (2R,4S)-1-Boc-4-fluoropyrrolidine-2-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: 97.0%

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (114676-69-6) → 1-(tert-butyl) 2-methyl (2R,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (647857-39-4)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at -78 - 20 ℃; for 42h;

Reference yield:

N-tert-butoxycarbonyl-trans-4-(trifluoromethylsulfonyloxy)-L-proline methyl ester (189160-59-6) → 1-(tert-butyl) 2-methyl (2R,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (647857-39-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 4 ℃;

DOI:10.1016/j.jfluchem.2008.06.024

Reference yield:

cis-hydroxy-D-proline (2584-71-6,30724-02-8) → 1-(tert-butyl) 2-methyl (2R,4S)-4-fluoropyrrolidine-1,2-dicarboxylate (647857-39-4)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride / 13 h / 0 - 20 °C

2: dmap; triethylamine / dichloromethane / 12 h / 20 °C

3: diethylamino-sulfur trifluoride / dichloromethane / 12 h / -78 - 20 °C / Inert atmosphere

With dmap; thionyl chloride; diethylamino-sulfur trifluoride; triethylamine; In dichloromethane;

upstream raw materials:

(2R,4R)-1-tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

N-tert-butoxycarbonyl-trans-4-(trifluoromethylsulfonyloxy)-L-proline methyl ester

(2R,4R)-4-Hydroxy-pyrrolidine-2-carboxylic acid methyl ester

cis-hydroxy-D-proline

Downstream raw materials:

C₅H₈FNO₂*ClH

6-[(2R,4S)-2-(2-chlorophenoxymethyl)-4-fluoropyrrolidin-1-yl]-9H-purine

tert-butyl (2R,4S)-2-(2-chlorophenoxymethyl)-4-fluoropyrrolidine-1-carboxylate

(2R,4S)-2-(2-chlorophenoxymethyl)-4-fluoropyrrolidine

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