HCID 86750088, compound → HCID 54398925, compound

HRID 964038Notes

Reaction equation

HRID 964038 reaction equation
[C:1]1([C@H:7]([N:9]2[CH2:16][C:15](=[N:17]O)[C:11]3([CH2:14][CH2:13][CH2:12]3)[C:10]2=[O:19])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Ni]>[NH2:17][CH:15]1[C:11]2([CH2:14][CH2:13][CH2:12]2)[C:10](=[O:19])[N:9]([C@@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH3:8])[CH2:16]1

Participants

4

Reactant 1

HCID 86750088HCID 86750088, compound

Product 1

HCID 54398925HCID 54398925, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8.75 g of 6-[1-(R)-phenylethyl]-8-hydroxyimino-5-oxo-6-azaspiro[3.4]octane in 300 ml of methanol there was added 26 ml of Raney nickel, and reduction was carried out under a hydrogen atmosphere at room temperature for 14.5 hr. The catalyst was removed by filtration and the solvent was removed under reduced pressure. By the same procedure, 1.65 g of 6-[1-(R)-phenylethyl]-8-hydroxyimino-5-oxo-6-azaspiro-[3.4]octane was reduced using 5 ml of Raney nickel. The crude products were combined and purified by column chromatography using a column containing 380 g of silica gel. From a fraction of an eluant of 1% (v/v) methanolic chloroform, 3.2 g of the less polar isomer of the titled compound was obtained and 1.8 g of the more polar isomer thereof along with 4.4 g of a mixture of the two isomers. 1H-NMR(CDCl3) δ ppm;1.48(3H, d, J=7.2 Hz), 1.70-2.40(6H, m), 2.50(1H, dd, J=7.2, 12.6 Hz), 3.20-3.52(2H, m), 5.50(1H, q, J=7.2 Hz), 7.32(5H, s).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed under reduced pressure
  3. custompurified by column chromatography
  4. additioncontaining 380 g of silica gel

Sources & evidence

ORD record
ord-17beb8fc52e247469fce4f9d6a79a8eb
Source dataset
uspto-grants-1998_06
Patent number
US05767127

Reaction notes

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