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

HRID 1906280Notes

Reaction equation

HRID 1906280 reaction equation
C([O:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11](OCC)=[O:12])[C:6]1=[O:16])(=O)C.[NH3:17]>CO>[OH:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([NH2:17])=[O:12])[C:6]1=[O:16]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 131713898ethyl (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.40 g of ethyl (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetate is treated with 45 ml of a saturated solution of ammonia in methanol. The mixture is left to stand at room temperature for 1 hour and then evaporated. The residue is treated four 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 (1:3).

Workup

  1. waitThe mixture is left
  2. customevaporated
  3. additionThe residue is treated four times with acetonitrile
  4. customin each case again evaporated

Sources & evidence

ORD record
ord-365a3e60194f42afa6f7bee2f0b715b6
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

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