tert-Butyldimethylsilyl chloride → HCID 22959074, compound

Participants

Reaction Steps

To a solution of (+)-trans-3-hydroxymethyl-4-(3-fluorophenyl)cyclopentan-1-one from Step D (6.23 g, 29.9 mmol) in methylene chloride (100 mL) was added DIPEA (16.0 mL, 11.6 g, 89.7 mmol) and t-butyldimethylsilyl chloride (6.80 g, 44.8 mmol). The reaction mixture was stirred at rt for 48 h, poured into aqueous sodium bicarbonate, and extracted three times with methylene chloride. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered and concentrated. The residue (12 g) was purified by FC (5% ethyl acetate in hexanes) to afford the title product (8.99 g) as a oil.

Provenance & Evidence