(3S,4S)-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

Base Information

• Chemical Name: (3S,4S)-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate
• CAS No.: 1009075-43-7
• Molecular Formula: C9H17FN2O2
• Molecular Weight: 204.245
• Hs Code.: 2933990090
• Mol file: 1009075-43-7.mol

Synonyms:tert-butyl (3S,4S)-3-amino-4-fluoropyrrolidine-1-carboxylate;

Chemical Property of (3S,4S)-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

Chemical Property:

• Boiling Point: 266.067 °C at 760 mmHg
• PKA: 8.29±0.40(Predicted)
• Flash Point: 114.714 °C
• PSA: 55.56000
• Density: 1.138 g/cm³
• LogP: 1.54070
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

99% ^*data from raw suppliers

(3S,4S)-tert-Butyl3-amino-4-fluoropyrrolidine-1-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (3S,4S)-tert-Butyl 3-Amino-4-fluoropyrrolidine-1-carboxylate, can be used in the synthesis of various pharmaceutical and biologically active compounds. It s used in the preparation of novel aminopyrrolidine derivatives, factor Xa inhibitors, acting as anticoagulants.

Technology Process of (3S,4S)-tert-Butyl 3-amino-4-fluoropyrrolidine-1-carboxylate

There total 5 articles about (3S,4S)-tert-Butyl 3-amino-4-fluoropyrrolidine-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: 99.2%

(3S,4S)-tert-butyl 3-(benzylamino)-4-fluoropyrrolidine-1-carboxylate → (3S,4S)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate (1009075-43-7,1174020-30-4,1260848-87-0,1441392-27-3,1363382-79-9,1431720-86-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol;

Reference yield:

(S)-3-azido-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester (913743-06-3) → (3S,4S)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate (1009075-43-7,1174020-30-4,1260848-87-0,1441392-27-3,1363382-79-9,1431720-86-3)

Guidance literature:

With platinum(IV) oxide; hydrogen; In methanol; at 20 ℃;

DOI:10.1016/j.ejmech.2008.12.025

Reference yield:

(3S,4S)-1-tert-butoxycarbonyl-trans-3-benzylamino-4-hydroxypyrrolidine (252574-03-1) → (3S,4S)-tert-butyl 3-amino-4-fluoropyrrolidine-1-carboxylate (1009075-43-7,1174020-30-4,1260848-87-0,1441392-27-3,1363382-79-9,1431720-86-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole; thionyl chloride; triethylamine / dichloromethane / 1 - 20 °C

2.1: rhodium(III) chloride hydrate; sodium periodate / acetonitrile; water; 1,2-dichloro-ethane / 18 h / 2 - 18 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Reflux

3.2: 2 h

4.1: hydrogen; palladium 10% on activated carbon / ethanol

With 1H-imidazole; sodium periodate; thionyl chloride; rhodium(III) chloride hydrate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;

upstream raw materials:

(S)-3-azido-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester

(3S,4S)-1-tert-butoxycarbonyl-trans-3-benzylamino-4-hydroxypyrrolidine

Refernces

• 1、 Zbinden, Katrin Groebke,Anselm, Lilli,Banner, David W.,Benz, Joerg,Blasco, Francesca,Decoret, Guillaume,Himber, Jacques,Kuhn, Bernd,Panday, Narendra,Ricklin, Fabienne,Risch, Philippe,Schlatter, Daniel,Stahl, Martin,Thomi, Stefan,Unger, Robert,Haap, Wolfgang. "Design of novel aminopyrrolidine factor Xa inhibitors from a screening hit". body text. p. 2787 - 2795. Retrieved 2009/10/17.