Aluminium lithium hydride → (RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol

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Reaction Steps

To a solution of 1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-one (211 mg, 0.5825 mmol) in THF (5 mL) was added LAH (1M in THF, 0.58 mL, 0.58 mmol) at 0° C. and stirred for 30 minutes. The reaction was quenched by an addition of aq. KF solution (135 mg in 0.5 mL of water). The mixture was stirred vigorously for 10 minutes followed by an addition of anhydrous sodium sulfate. The insoluves were removed by filtration through a cotton pad and the cake was washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (heptane/ethyl acetate 3:1 to 1:1) yielding (RS)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol as a light yellow oil with ES-MS m/e: 364.1 (M'H+) and (SR)-1-[(3RS,4SR)-1-benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-propan-1-ol as a light yellow oil. ES-MS m/e: 364.1 (M+H+).

Provenance & Evidence