HCID 86750088, compound → HCID 54398925, compound

Participants

Reaction Steps

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).

Provenance & Evidence