tert-Butyl 4-((2-amino-5-chloro-3-nitrobenzoyloxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate → tert-Butyl 4-((2,3-diamino-5-chlorobenzoyloxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 4-((2-amino-5-chloro-3-nitrobenzoyloxy)methyl)-4-(4-fluorophenyl)piperidine-1-carboxylate (700 mg, 1.4 mmol) in ethyl acetate (20 mL) under nitrogen was added palladium (10% on carbon, 140 mg). The flask was flushed with hydrogen and shaken under 60 psi of hydrogen overnight. The reaction was filtered through celite and concentrated to give 715 mg (quant.) as a foam semi-solid which was used without purification. tR=3.19 (Sunfire C18 4.6×50 mm, A=90% H2O/10% ACN, B=90% ACN/10% H2O, Modifier 0.1% TFA, 0.00 min=0% B, 4.0 min=100% B, 5.0 min=100% B, Flow rate=4 mL/min. Mass spec.: 377.88 (MH-Boc)+.

Provenance & Evidence