Aluminium lithium hydride → HCID 67190388, compound

Participants

Reaction Conditions

Reaction Steps

A slurry of LiAlH4 (2.99 g, 78.5 mmol, 2.0 equiv) in THF (100 mL) was cooled to −78° C. A solution of the above (1S,3S,4S)-ethyl 3-(tert-butyldimethylsilyloxy)-4-fluorocyclopentanecarboxylate in THF (50 mL) was added over 20 min, and the mixture was stirred at −78° C. for 0.5 h. Analysis by tlc showed consumption of the ester. The mixture was allowed to warm to 0° C., then brine (10 mL) was added dropwise over a 15 min, followed by ˜20 g of Celite. The thick slurry was diluted with EtOAc and allowed to stir for 0.5 h. The mixture was filtered through a pad of Celite. The filter cake was washed with additional EtOAc. The resulting clear solution was dried over Na2SO4, filtered, and evaporated. This afforded ((1S,3S,4S)-3-(tert-butyldimethylsilyloxy)-4-fluorocyclopentyl)methanol 7.24 g (76% yield).

Provenance & Evidence