HCID 86749079, compound → HCID 15284548, compound

HRID 2211211Notes

Reaction equation

HRID 2211211 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]([C@@H: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 15284548HCID 15284548, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In 300 ml of methanol was dissolved 11.5 g of 3,3-dimethyl-4-hydroxyimino-1-[1-(R)-phenylethyl]-Pyrrolidin-2-one, and about 20 ml of Raney nickel washed with methanol was added to the solution. Reduction was conducted at room temperature for 16 hours in an egg-plant type flask. The catalyst was removed by filtration, and the solvent of filtrate was removed under reduced pressure. The residue was subjected to silica gel (400 g) column chromatography using a 30:1 (by volume) mixture of chloroform and methanol as an eluent to yield 3.75 g of Fraction 1 (lower polar material) and 10.2 g of a mixture of Fraction 1 and Fraction 2 (higher polar material).

Workup

  1. washwashed with methanol
  2. additionwas added to the solution
  3. customThe catalyst was removed by filtration
  4. customthe solvent of filtrate was removed under reduced pressure
  5. additiona 30:1 (by volume) mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-9fff0857d4ee40c7a3dfb312a3ea9fcb
Source dataset
uspto-grants-1995_10
Patent number
US05463053

Reaction notes

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