Lithium borohydride → 4-[(3SR,4RS)-1-benzyl-4-((RS)-1-hydroxy-ethyl)-pyrrolidin-3-yl]-benzonitrile

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Reaction Steps

To a solution of 4-((3SR,4RS)-4-acetyl-1-benzyl-pyrrolidin-3-yl)-benzonitrile (IV-5) (IV-5) (6.30 g, 20.7 mmol) in MeOH (300 mL) at RT were added portion wise LiBH4 (9.49 g, 0.43 mol). Stirring was continued for overnight, and the reaction mixture was carefully quenched by addition of aq. NH4Cl, concentrated under vacuo and the product extracted with EtOAC. The combined organic phases were dried on Na2SO4 and concentrated under vacuo. The two diastereoisomeres were separated by column chromatography (SiO2, EtOAc/H, 1:1) to yield 4-[(3SR,4RS)-1-benzyl-4-((RS)-1-hydroxy-ethyl)-pyrrolidin-3-yl]-benzonitrile (V-B-5) 1.35 g (21%) as a colorless oil ES-MS m/e: 307.2 (M+H+) and 4-[(3SR,4RS)-1-benzyl-4-((SR)-1-hydroxy-ethyl)-pyrrolidin-3-yl]-benzonitrile (V-A-5) 1.30 g (20%) as a colorless oil ES-MS m/e: 307.2 (M+H+).

Provenance & Evidence