Sodium borohydride → 4-bromo-6,6-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridin-7-ol

Participants

Reaction Steps

To a solution of 4-bromo-6,6-dimethyl-5H-cyclopenta[c]pyridin-7(6H)-one (1.1 g, 4.58 mmol) in MeOH (25 mL) was added NaBH4 (261.3 mg, 6.88 mmol) portion wise. The resulting mixture was stirred for 1 h before it was quenched with water. The solution was concentrated in vacuo and the residue was extracted between EtOAc and H2O (20 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give a crude title product. MS: 243.7 (M+H+, 1 Br).

Provenance & Evidence