Hydrochloric Acid → (1S,3S)-N-[2,2-difluoro-2-(4-methylphenyl)ethyl]cyclopentane-1,3-diamine

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Reaction Steps

1M borane in THF (20 mL, 20 mmol) was added slowly to a stirred solution of N-[(1S,3S)-3-aminocyclopentyl]-2,2-difluoro-2-(4-methylphenyl)acetamide (1.006 g, 3.749 mmol) in dry THF (20 mL) at 0° C. The reaction mixture was warmed to rt. and then was heated to 70° C. for 1 h. The reaction mixture was cooled, quenched with 6N HCl (2.5 mL, 15 mmol) and stirred at rt for 16 h. Aqueous sodium carbonate was added to pH=11, and the mixture was extracted with EtOAc, dried (MgSO4), filtered and concentrated. The resulting oil was purified by silica gel chromatography (eluting with 1.2% NH4OH/10.8% MeOH/CHCl3) to give the title compound as a pale yellow oil (627 mg): MS=255.4 (M+1).

Provenance & Evidence