Triethylamine → 1-(2-Hydroxy-2-phenyl-1-pyridin-2-ylethyl)pyrrolidin-2-one

HRID 1170393Notes

Reaction equation

HRID 1170393 reaction equation
C(N(CC)CC)C.Cl[CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13].[NH2:15][CH:16]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)[CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:18].[OH-].[Na+]>CN(C=O)C>[OH:18][CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:16]([N:15]1[CH2:9][CH2:10][CH2:11][C:12]1=[O:13])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 783704-Chlorobutyryl chlorideHCID 675240462-Amino-1-phenyl-2-pyridin-2-ylethanol

Product 1

HCID 675241331-(2-Hydroxy-2-phenyl-1-pyridin-2-ylethyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

35 ml (252 mmol) of triethylamine and 11.3 ml (101 mmol) of 4-chlorobutyryl chloride were successively added dropwise to a solution of 21.6 g (101 mmol) of 2-amino-1-phenyl-2-pyridin-2-ylethanol in 50 ml of DMF at 50° C. After 1 h at room temperature, 48.4 g of sodium hydroxide were added, and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into ice-water and extracted with methylene chloride, and the organic phases were washed with water and sodium bicarbonate solution. Chromatography on silica gel with ethyl acetate/ethanol 20:1 resulted in isolation of 3.0 g each of the syn- and anti-diastereomer of 1-(2-hydroxy-2-phenyl-1-pyridin-2-ylethyl)pyrrolidin-2-one in pure form. The relative stereochemistry was assigned by X-ray spectroscopy.

Workup

  1. extractionextracted with methylene chloride
  2. washthe organic phases were washed with water and sodium bicarbonate solution

Sources & evidence

ORD record
ord-37cf0ee609994af7b6007ab7aae266b2
Source dataset
uspto-grants-2010_11
Patent number
US07825264B2

Reaction notes

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