tert-butyl (2S,4R)-2-(aMinoMethyl)-4-fluoro-1-pyrrolidinecarboxylate

Base Information

• Chemical Name: tert-butyl (2S,4R)-2-(aMinoMethyl)-4-fluoro-1-pyrrolidinecarboxylate
• CAS No.: 1138324-46-5
• Molecular Formula: C₁₀H₁₉FN₂O₂
• Molecular Weight: 218.271
• Mol file: 1138324-46-5.mol

Synonyms:tert-butyl (2S,4R)-2-(aMinoMethyl)-4-fluoro-1-pyrrolidinecarboxylate;tert-butyl (2S,4R)-2-(aminomethyl)-4-fluoropyrrolidine-1-carboxylate;(2S,4R)-tert-Butyl 2-(aminomethyl)-4-fluoropyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2S,4R)-2-(aMinoMethyl)-4-fluoro-1-pyrrolidinecarboxylate

Chemical Property:

• PSA: 55.56000
• LogP: 1.93080
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99%, ^*data from raw suppliers

tert-Butyl(2S,4R)-2-(Aminomethyl)-4-fluoro-1-pyrrolidinecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of tert-butyl (2S,4R)-2-(aMinoMethyl)-4-fluoro-1-pyrrolidinecarboxylate

There total 6 articles about tert-butyl (2S,4R)-2-(aMinoMethyl)-4-fluoro-1-pyrrolidinecarboxylate 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:

tert-butyl (2S,4R)-2-(azidomethyl)-4-fluoropyrrolidine-1-carboxylate (1138324-45-4) → tert-butyl (2S,4R)-2-(aminomethyl)-4-fluoropyrrolidinecarboxylate (1138324-46-5,1033245-12-3)

Guidance literature:

With 5% Pd(II)/C(eggshell); hydrogen; In ethanol;

DOI:10.1016/j.bmcl.2010.12.078

Reference yield:

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester (74844-91-0,114676-69-6,135042-17-0,227935-38-8,102195-79-9) → tert-butyl (2S,4R)-2-(aminomethyl)-4-fluoropyrrolidinecarboxylate (1138324-46-5,1033245-12-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 - 20 °C

3.1: triethylamine / dichloromethane / 4.5 h / 0 - 20 °C

4.1: sodium azide / N,N-dimethyl-formamide / 24 h / 60 °C

5.1: triphenylphosphine / tetrahydrofuran / 8 h / 65 °C

5.2: 16 h / 65 °C

With sodium azide; diethylamino-sulfur trifluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.joc.5b00283

Reference yield:

methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate (203866-18-6) → tert-butyl (2S,4R)-2-(aminomethyl)-4-fluoropyrrolidinecarboxylate (1138324-46-5,1033245-12-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 - 20 °C

2.1: triethylamine / dichloromethane / 4.5 h / 0 - 20 °C

3.1: sodium azide / N,N-dimethyl-formamide / 24 h / 60 °C

4.1: triphenylphosphine / tetrahydrofuran / 8 h / 65 °C

4.2: 16 h / 65 °C

With sodium azide; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/acs.joc.5b00283

upstream raw materials:

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

(2S,4S)-N-tert-butoxycarbonyl-4-hydroxyproline methyl ester

methyl (2S,4R)-N-(tert-butyloxy)carbonyl-4-fluoropyrrolidine-2-carboxylate

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Downstream raw materials:

C₃₃H₄₄F₂N₆O₅

C₃₂H₄₂F₂N₆O₅

C₃₁H₄₀F₂N₆O₅

C₃₂H₄₀F₂N₆O₅

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