1-t-Butoxycarbonyl-4-(3-(3,5-difluorophenyl)prop-2-enyl) piperidine → 1-t-Butoxycarbonyl-4-(3-(3,5-difluorophenyl)propyl) piperidine

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Reaction Steps

A mixture of 1-t-butoxycarbonyl-4-(3-(3,5-difluorophenyl) prop-2-enyl)piperidine (from EXAMPLE 95, Step C) and 50 mg of 10% palladium on carbon in MeOH (10 mL) was hydrogenated at 50 psi for 2 h. The suspension was filtered though Celite, the cake washed with MeOH and the filtrate was concentrated. Flash chomatography using 0-15% EtOAc in hexanes (v/v) as the eluant afforded the title compound: 1H NMR (500 MHz ) δ 1.10 (dq, J=4.4, 8.2, 21), 1.25-1.30 (21), 1.37-1.45 (m, 1H), 1.47 (s, 9H), 1.62-1.67 (4H). 2.59 (t, J=7.8, 2H), 2.62-2.78 (2H), 4.08 (bs, 2H), 6.61-6.70 (3H).

Provenance & Evidence