Aluminium lithium hydride → (S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

The compound of Example 10D (6.45 g, 16 mmol) was dissolved in 30 mL of ether and cooled to −30° C.; 35 mL of a 1 N solution of lithium aluminum hydride in ether was added at a rate so as to maintain a constant temperature and a modest rate of gas evolution. The mixture was stirred at −30° C. for 10 minutes, and then it was warmed to 0° C. for 1 hour. The reaction was quenched by the careful addition of ethyl acetate (Caution! Vigorous gas evolution) and stirred for 10 minutes, then quenched with a solution of Rochelle's salt. The resultant mixture was partitioned between ethyl acetate and water; the organic phase was washed with brine and dried over Na2SO4. The solvents were removed in vacuo, and the residue was purified by chromatography on an Analogix Intelliflash 280™, eluting with a gradient of 5% to 30% ethyl acetate in hexanes.

Provenance & Evidence