HCID 86749079, compound → 4-Amino-3,3-dimethyl-1-(1-phenylethyl)-2-pyrrolidinone

HRID 1445276Notes

Reaction equation

HRID 1445276 reaction equation
[CH3:1][C:2]1([CH3:18])[C:6](=[N:7]O)[CH2:5][N:4]([C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:3]1=[O:17]>CO.[Ni]>[NH2:7][CH:6]1[CH2:5][N:4]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:3](=[O:17])[C:2]1([CH3:1])[CH3:18]

Participants

4

Reactant 1

HCID 86749079HCID 86749079, compound

Product 1

HCID 193543084-Amino-3,3-dimethyl-1-(1-phenylethyl)-2-pyrrolidinoneYield 123.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8.75 g of 3,3-dimethyl-4-hydroxyimino-1-[1-(R)-phenylethyl]-pyrrolidin-2-one in 300 ml of methanol there was added 20 ml of Raney-nickel, and reduction was carried out under a hydrogen atmosphere at room temperature for 16 hr (H2 pressure: 1 atm). The catalyst was removed by filtration and the solvent of the filtrate was removed under reduced pressure. The residue was purified through column chromatography using a column filled with 300 g of silica gel. From a fraction eluted with a mixture of methanol and chloroform (1:30, v/v), 3.75 g of the less polar isomer of the titled compound was obtained along with 10.2 g of a mixture of the less polar and more polar titled compound.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. customThe residue was purified through column chromatography
  4. additionfilled with 300 g of silica gel
  5. washFrom a fraction eluted with a mixture of methanol and chloroform (1:30, v/v), 3.75 g of the less polar isomer of the titled compound

Sources & evidence

ORD record
ord-90a369725bef4cf68af44effb01d62bc
Source dataset
uspto-grants-2010_02
Patent number
USRE041149E1

Reaction notes

Loading…