Sodium Bicarbonate → HCID 68665485, compound

Participants

Reaction Steps

To a solution of (1S,3R)-3-(4-bromophenyl)cyclopentanol (503 mg, 2.09 mmol) in 10 mL of CH2Cl2 at −78° C. was added (bis(2-methoxyethyl)amino)sulfur tri fluoride (Deoxo-Fluor, 462 μL, 2.50 mmol). The mixture was allowed to gradually warm up to rt overnight and then poured into sat'd NaHCO3 (20 mL). The aqueous layer was extracted with CH2Cl2 (3×20 mL). The organic layer was dried over MgSO4 and concentrated. Chromatography on a Biotage 40+S cartridge using hexanes as the eluant afforded 383 mg (76%) of the title compound: 1H NMR δ 1.53-1.78 (m, 2H), 1.95-2.39 (m, 4H), 3.35 (m, 1H), 5.19-5.32 (m, 1H), 7.09 (d, J 8.5, 2H), 7.40 (d, J=8.2, 2H).

Provenance & Evidence