Sodium Hydroxide → HCID 68666307, compound

Participants

Reaction Steps

To a solution of (1R,3R)-3-(4-bromophenyl)cyclopentyl acetate (CARBOXYLIC ACID 8, Step B, 536 mg, 1.9 mmol) in 5.0 mL of EtOH was added sodium hydroxide (1.9 mL, 5.0 N). After stirring at rt for 30 min, solvent was removed and the residue was partitioned between sat'd NaHCO3 (50 mL) and CH2Cl2 (50 mL). The aqueous layer was separated and extracted with CH2Cl2 (2×50 mL). Organic layers were combined, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+M cartridge using 7:3 v/v hexanes/EtOAc as the eluant afforded 445 mg (97%) of the title compound: 1H NMR δ 1.49 (br. s, 1H), 1.56-1.81 (m, 2H), 2.05-2.27 (m, 4H), 3.35 (m, 1H), 4.52 (m, 1H), 7.09 (d, J=8.2, 2H), 7.40 (d, J=8.3, 2H).

Provenance & Evidence