Ammonia → tert-Butyl (3R)-3-(aminomethyl)pyrrolidine-1-carboxylate

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Reaction Steps

A mixture of tert-butyl (3R)-3-cyano-1-pyrrolidinecarboxylate (preparation 79) (1.60 g, 8.13 mmol) and Raney® Nickel (1 g) in 0.88 ammonia (20 ml) and ethanol (150 ml), was hydrogentaed at 60 psi and room temperature for 8 hrs. The mixture was filtered through Arbocel®, and the filtrate concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (100:0:0 to 90:10:1) to yield the desired product as an oil, (1.59 g, 98%).

Provenance & Evidence