Sodium borohydride → 4-(Pyrrolidin-1-ylmethyl)benzylamine

Participants

Reaction Conditions

Reaction Steps

Dissolve 4-(pyrrolidin-1-ylmethyl)-benzonitrile (918 mg, 4.93 mmol) in methanol (32 mL). Add cobalt(II) chloride hexahydrate (2.7 g, 9.87 mmol) and stir for 20 min. Cool the mixture to 0° C., and carefully add sodium borohydride (1.86 g, 49.3 mmol) in small batches. Stir the mixture for 1.5 h at room temperature. Quench the mixture with water and partition between water and chloroform. Extract the aqueous phase three times with chloroform/iso-propanol (3:1). Dry the combined organic extracts over MgSO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (80 g) eluting with a gradient of DCM/(chloroform:methanol:concentrated NH4OH 80:18:2) (1:0 over 5 min, 19:1 over 5 min, 9:1 over 5 min, 85:15; 50 mL/min) to give the title compound (421 mg, 45%). MS (ES+) m/z: 191 (M+H)+,

Provenance & Evidence