Trifluoroacetic acid → (2R,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid cyclopropylamide

HRID 1839839Notes

Reaction equation

HRID 1839839 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@@H:9]1[C:14](=[O:19])[NH:15][CH:16]1[CH2:18][CH2:17]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:16]1([NH:15][C:14]([C@H:9]2[CH2:10][C@@H:11]([OH:13])[CH2:12][NH:8]2)=[O:19])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69741572(2R,4R)-2-cyclopropylcarbamoyl-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 28943484(2R,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid cyclopropylamideYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R,4R)-2-Cyclopropylcarbamoyl-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (5 g) was deprotected using 50 mL of 30% TFA in DCM at rt for 2 hours to give 3 g of (2R,4R)-4-hydroxy-pyrrolidine-2-carboxylic acid cyclopropylamide as a light yellow oil.

Workup

  1. customat rt
  2. customfor 2 hours

Sources & evidence

ORD record
ord-32eceb6df9d34c85af99f07d0247bcf0
Source dataset
uspto-grants-2004_01
Patent number
US06677368B2

Reaction notes

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