m-Chloroperbenzoic acid → HCID 13632649, compound

Participants

Reaction Steps

To a stirred mixture of 11.65 g of 1-(1-hydroxy-1-methylethyl)-3-methyl-3-cyclopentene-1-carbonitrile in 700 ml of methylene chloride and 210 ml of aqueous sodium bicarbonate was added portionwise at 25°-35° C. 15.3 g of 85% m-chloroperbenzoic acid. After stirring overnight, the phases were separated and the organic phase was washed successively with 200 ml of 1N sodium hydroxide, 200 ml of water and 200 ml of saturated aqueous sodium chloride, dried (MgSO4), and concentrated in vacuo to leave 14.2 g of a colorless oil, as a 1.2;1.0 mixture of diastereomeric epoxides. These diastereomers were separated by flash silica gel column chromatography using 2:8:40 tetrahydrofuran/ethyl acetate/hexane as eluent to give 5.1 g of the less polar (1α,3β,5α) isomer as a colorless oil and using 2:15:33 ratio of the same solvents to give 5.4 g of the more polar (1α,3α,5α)isomer as a colorless oil.

Provenance & Evidence