Methyl [3,5-bis(trifluoromethyl)benzyl][(5'-isopropyl-2'-methoxy-4-nitrobiphenyl-2-yl)methyl]carbamate → Methyl [(4-amino-5'-isopropyl-2'-methoxybiphenyl-2-yl)methyl][3,5-bis(trifluoromethyl)benzyl]carbamate

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Reaction Steps

A solution of the methyl [3,5-bis(trifluoromethyl)benzyl][(5′-isopropyl-2′-methoxy-4-nitrobiphenyl-2-yl)methyl]carbamate from Example 8 (0.31 g, 0.53 mmol) in MeOH (10 ml) was charged with a catalytic amount Pd/C and hydrogen at 40 psi for 1 h. The mixture was filtered through Celite and the filtrate was concentrated. The title compound was obtained by flash column chromatography using 3:7 EtOAc/hexane as the eluant. 1H NMR (CDCl3, 500 MHz) δ 7.72 (m, 1H), 7.50 (s, 1H), 7.30 (s, 1H), 7.16 (m, 1H), 7.03 (d, J=8.0 Hz, 1H), 6.94 (s, 1H), 6.82 (m, 1H), 6.69 (dd, J=8.5, 2.5 Hz, 1H), 6.58 (m, 1H), 4.18-4.30 (m, 4H), 3.75 (s, 3H), 3.65 (s, 3H), 2.83 (m, 1H), 1.20 (s, 6H). LC-MS (M+1): 555.3 (3.58 min).

Provenance & Evidence