Trifluoroacetic acid → 4,4-Difluoroproline

HRID 1805154

Reaction equation

HRID 1805154 reaction equation
C(OC([N:8]1[CH2:12][C:11]([F:14])([F:13])[CH2:10][C@H:9]1[C:15]([OH:17])=[O:16])=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:13][C:11]1([F:14])[CH2:12][NH:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22977458(2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid

Product 1

HCID 152161024,4-Difluoroproline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-1-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid (500 mg, 2.0 mmol) was dissolved in dichloromethane and treated dropwise with TFA (227 mg, 153 μL, 2 mmol). The reaction was stirred for 3 h at room temperature, the solvents evaporated to obtain (S)-4,4-difluoropyrrolidine-2-carboxylic acid, which was used in the next step without further purification. LC/MS: m/z 152.2 (M+H)+ at 0.53 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customthe solvents evaporated

Sources & evidence

ORD record
ord-0494779c1a96490985c74e0916850bcc
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Linked notes

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