Hydrochloric Acid → HCID 56636518, compound

Participants

Reaction Conditions

Reaction Steps

In a flow of argon, to a solution cooled to -78° C., of 13.6 g of (1R,2S,3S)-2-benzyloxymethyl-1-(2-tetrahydropyranyloxy)-3-[2-(p-toluenesulphonyloxy)ethyl]cyclopentane (prepared in Reference Example 5) in 30 ml of dry tetrahydrofuran, 12.5 ml of a 3M solution of ethyl magnesium bromide in diethyl ether was added over a period of 10 min; to the solution, 5 ml of a solution of 8.4 g of lithium chloride and 13.4 g of cupric chloride in 1 l of tetrahydrofuran was added dropwise over a period of 5 min. The mixture was stirred further for 1.5 hrs at the same temperature, for 2 hrs at 0° C., and for 16 hrs at room temperature. The reaction solution was poured into a mixture of 70 ml of 1N hydrochloric acid, ice and 150 ml of diethyl ether, and the ether layer separated was washed with an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulphate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (5:1) as eluent to give 8.63 g of the title compound having the following physical characteristics, in a 89.8% yield.

Provenance & Evidence