Hydrochloric Acid → (3S)-3-(4-bromophenyl)cyclopentanol

Participants

Reaction Conditions

Reaction Steps

To a solution of (3R)-3-(4-Bromophenyl)cyclopentanone (1.14 g, 4.77 mmol, CARBOXYLIC ACID 4, Step A) in 10 mL of CH2Cl2 at −78° C. was added diisobutylaluminum hydride (7.2 mL, 1.0 M in CH2Cl2). The mixture was stirred at −78° C. for 1 hr and then 5.0 mL of sat'd Rochelle's salt aqueous solution was added. The mixture was poured into diluted HCl solution and extracted with CH2Cl2 (3×10 mL). Organic layers were combined, washed with sat'd NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated to give 1.16 g (100%) of the title compound as a 1:1 ratio diastereomeric mixture, which cannot be separated by chromatography.

Provenance & Evidence