Ammonia → (2S,4S)-4-hydroxypyrrolidine-2-carboxamide

HRID 1807670Notes

Reaction equation

HRID 1807670 reaction equation
Cl.C[O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][NH:7]1)=O.[NH3:12]>CO>[OH:11][C@@H:9]1[CH2:8][NH:7][C@H:6]([C:4]([NH2:12])=[O:3])[CH2:10]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12764092cis-4-Hydroxy-L-proline methyl ester hydrochloride

Product 1

HCID 2452260(2S,4S)-4-hydroxypyrrolidine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2S,4S)-4-hydroxy-pyrrolidine-2-carboxylic acid methyl ester hydrochloride (1 g) in a 7M solution of ammonia in MeOH (10 ml) was stirred for 18 h then evaporated and triturated with Et2O. The residue was dissolved in the minimum volume of hot MeOH and stood at 4° C. for 4 h. The title compound was isolated by filtration as a white solid.

Workup

  1. customthen evaporated
  2. customtriturated with Et2O
  3. dissolutionThe residue was dissolved in the minimum volume of hot MeOH

Sources & evidence

ORD record
ord-fd193be946c7456a9a2ca9cfd72b8df7
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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