Lithium borohydride → [(3RS,4SR)-3-(3,4-dichloro-phenyl)-4-((RS)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-(6-methoxy-pyridin-3-yl)-methanone

Participants

Reaction Steps

To a stirred solution of 1-[(3SR,4RS)-4-(3,4-dichloro-phenyl)-1-(6-methoxy-pyridine-3-carbonyl)-pyrrolidin-3-yl]-ethanone (XIV-1) (0.64 g, 1.60 mmol) in MeOH (10 mL) at −78° C. was added LiBH4 (0.047 g, 1.70 mmol). The temperature was slowly raised to RT (over 1 hour), and the reaction mixture was quenched by addition of H2O. The product was extracted with EtOAc, the combined organic phases were dried over Na2SO4. The two diastereoisomers were separated by column chromatography (SiO2) to yield 0.15 g (23%) of [(3RS,4SR)-3-(3,4-dichloro-phenyl)-4-((RS)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-(6-methoxy-pyridin-3-yl)-methanone (XV-A-1) as a white solid ES-MS m/e: 395.3 (M+H+) and 0.48 g (75%) of [(3RS,4SR)-3-(3,4-dichloro-phenyl)-4-((SR)-1-hydroxy-ethyl)-pyrrolidin-1-yl]-(6-methoxy-pyridin-3-yl)-methanone (XV-B-1) as a white solid ES-MS m/e: 395.3 (M+H+).

Provenance & Evidence