1-(1H-Imidazol-1-yl)ethanone → (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide

HRID 1632566Notes

Reaction equation

HRID 1632566 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:21])[CH2:13][N:14]1[CH2:18][CH2:17][CH:16]([OH:19])[C:15]1=[O:20].[C:22](N1C=CN=C1)(=[O:24])[CH3:23]>C1(C)C=CC=CC=1>[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:21])[CH2:13][N:14]1[CH2:18][CH2:17][CH:16]([O:19][C:22](=[O:24])[CH3:23])[C:15]1=[O:20]

Participants

4

Reactant 2

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 3069833cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.594 g of (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide is boiled at reflux for 4 hours with 0.222 g of N-acetylimidazole in 10 ml of toluene. The mixture is chromatographed over 21 g of aluminum oxide (activity grade III, neutral). The (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with methylene chloride has a melting point of 120°-121° after crystallization from diethyl ether.

Workup

  1. customThe mixture is chromatographed over 21 g of aluminum oxide (activity grade III, neutral)
  2. washThe (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetamide which is eluted with methylene chloride
  3. customafter crystallization from diethyl ether

Sources & evidence

ORD record
ord-8699c9d5ab3749c6965c6722c1bf2dd5
Source dataset
uspto-grants-1984_10
Patent number
US04476308

Reaction notes

Loading…