Ethyl Acetate → HCID 19887970, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2.26 g of the compound of Example 2 in 54 ml of tetrahydrofuran which was cooled to -78° C. was added 14.5 ml of a 1.5M solution of diisobutylaluminum hydride in toluene. The reaction mixture was then stirred for 2 hours, while maintaining the temperature at -78° C., after which time it was warmed to room temperature. The mixture was then stirred for an additional 22 hours, after which time it was poured into a mixture of 100 ml of ethyl acetate and 100 ml of a saturated aqueous ammonium chloride solution. The resultant mixture was then filtered through Celite and the filtrate was extracted with a mixture of ethyl acetate and water. The organic layers were then combined, dried and evaporated to afford the crude residue which was chromatographed on silica gel employing a mixture of hexane and isopropyl alcohol in a ratio of 3:1 as the eluent to yield the 1α, 2α, 5β and 1α, 2α, 5α isomers of the title compound, the former of which had a m.p. of 126°-128° C., and the latter of which had a m.p. of 138°-140° C.

Provenance & Evidence