Chloroform → HCID 53257409, compound

Participants

Reaction Steps

A solution of 945 mg epoxide (−)-cis-verbenole (1R,2R,4S,5R,6S)-2 ([α]D25=−85.6 (c0.82, CHCl3)) in 12 ml methylene chloride was added, stiffing continuously, into a suspension of 2 g K10 (Fluka) clay (calcinated for 3 hours under 110° C.) in 15 ml of methylene chloride. The reaction mixture was stirred for 1 hour under room temperature. The catalyst was filtered, rinsed by ethyl acetate, the solvent was evaporated. The residue was separated by column chromatography using SiO2 (60-200μ; Merck), a solution of diethyl ether in hexane 5 to 100% was used as an eluent. 270 mg (29%) of (1R,2R,6s)-1a (ee 94%, ([α]D27=−84.0 (c 3.47, CHCl3)) was obtained as a result. Enantiomeric purity of the compound 1a was evaluated by the data of gas-liquid chromatography with mass spectroscopy in chiral column.

Provenance & Evidence