Ammonium Hydroxide → 1-Pyrrolidineacetamide, 3-hydroxy-2-oxo-, (+-)-

HRID 1906266Notes

Reaction equation

HRID 1906266 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8](OCC)=[O:9])[C:3]1=[O:13].[OH-].[NH4+:15]>C(#N)C>[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([NH2:15])=[O:9])[C:3]1=[O:13]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 13385945ethyl (R/S)-2-(3-hydroxy-2oxo-1-pyrrolidinyl)acetate

Product 1

HCID 30698541-Pyrrolidineacetamide, 3-hydroxy-2-oxo-, (+-)-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.50 g of ethyl (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetate are treated with 11.5 ml of approximately 25% ammonium hydroxide solution, whereupon the mixture is stirred at room temperature for 1 hour. The mixture is treated with acetonitrile and evaporated. The residue is treated five times with acetonitrile and in each case again evaporated. There is obtained (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide which melts at 163°-164° after recrystallization from methanol/diethyl ether (1:2).

Workup

  1. customevaporated
  2. additionThe residue is treated five times with acetonitrile
  3. customin each case again evaporated

Sources & evidence

ORD record
ord-a8cc5270fcce4e1bb5874422393a6e80
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

Loading…