(1R,2S)-[2-({[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-methyl)-cyclohexyl]-carbamic Acid Benzyl Ester → (1R,2S)-2-({[3-(4-fluorophenyl)-propyl]-methyl-amino}-methyl)-cyclohexylamine

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Reaction Steps

A mixture of (1R,2S)-[2-({[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-methyl)-cyclohexyl]-carbamic acid benzyl ester (400 mg, 970 μM) and 20% palladium hydroxide on charcoal (Pearlman's catalyst, 200 mg) in methanol (25 mL) was shaken in a pressure bottle under a hydrogen atmosphere (55 psig) for 16.5 hours. The mixture was filtered and the solid was washed with methanol. The combined filtrates were concentrated under vacuum to provide a tan viscous oil (268 mg, quantitative), used without further purification.

Provenance & Evidence