Diisobutylaluminum hydride → HCID 12073621, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution consisting of (3aR,4S,5S,6aS)-4-((tert-butyldiphenylsilyloxy)methyl)-5-fluorohexahydro-2H-cyclopenta[b]furan-2-one (prepared in Step A, 26.6 g, 64.6 mmol) in anhydrous THF (1 L) cooled to −78° C. was added DIBAL-H (1 M solution in THF; 200 mL) dropwise. The reaction mixture was stirred at −78° C. and reaction progress was monitored by TLC. After 2 hours, the reaction mixture was quenched by the addition of 2:1 THF-water at −78° C. and the reaction mixture was allowed to warm to room temperature with stirring until precipitated aluminum salts settled out of solution. The aluminum salts were removed by filtration through a sintered glass fritted filter funnel and the filtrate was evaporated to dryness to afford the title intermediate (26 g) The crude intermediate was carried on with no further purification.

Provenance & Evidence