Methyl {[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]carbamate → Methyl[3-amino-5-(trifluoromethyl)benzyl]{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Participants

Reaction Steps

A solution of methyl{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}[3-nitro-5-(trifluoromethyl)benzyl]carbamate (174 mg, 0.03 mmol) (Example 22) and PtO2 (10 mg) in THF (10 mL) was placed under hydrogen. The reaction was stirred at room temperature under hydrogen for two hours. The reaction was then diluted with hexanes (25 mL), loaded on a silica gel column, and purified with 15% EtOAc/hexanes to afford methyl[3-amino-5-(trifluoromethyl)benzyl]{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate. Rf=0.31 (25% EtOAc/hexanes). LCMS=555.3 (M+1)+. 1H NMR (CDCl3, 600 MHz) δ 7.59-6.28 (m, 9H), 4.48-3.62 (m, 12H), 2.87 (m, 1H), 1.22 (broad singlet, 6H).

Provenance & Evidence