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

HRID 1087067Notes

Reaction equation

HRID 1087067 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-021b6f3c6e5e4d10a086d5b52e778222
Source dataset
uspto-grants-1991_07
Patent number
US05034402

Reaction notes

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