Ammonia → cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

HRID 1906290Notes

Reaction equation

HRID 1906290 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:8])[N:3]1[CH2:9][CH2:10][NH:11][C:12](=[O:24])[CH2:13][N:14]1[CH2:18][CH2:17][CH:16]([O:19]C(=O)C)[C:15]1=[O:23].N>CO>[CH3:8][C@H:4]1[CH2:5][CH2:6][CH2:7][C@@H:2]([CH3:1])[N:3]1[CH2:9][CH2:10][NH:11][C:12](=[O:24])[CH2:13][N:14]1[CH2:18][CH2:17][CH:16]([OH:19])[C:15]1=[O:23]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 53715870(R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide

Product 1

HCID 3069833cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.3 g of (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide is stirred at room temperature for 2 hours in 30 ml of a saturated solution of ammonia in methanol. After evaporation of the methanol, the residue is treated three times with toluene and in each case again evaporated. After trituration in diethyl ether, there is obtained (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide of melting point 129°-130°.

Workup

  1. customAfter evaporation of the methanol
  2. additionthe residue is treated three times with toluene
  3. customin each case again evaporated

Sources & evidence

ORD record
ord-f190bc9f352a4e7b90351978d0407346
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

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