4-Trifluoromethylbenzyl chloroformate → 4-(Trifluoromethyl)benzyl (1R,2R)-2-((S)-1-(4-cyanophenyl)piperidin-3-ylamino)cyclohexylcarbamate

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Reaction Steps

4-(Trifluoromethyl)benzyl (1R,2R)-2-((S)-1-(4-cyanophenyl)piperidin-3-ylamino)cyclohexylcarbamate was synthesized using 4-((S)-3-((1R,2R)-2-aminocyclohexylamino)piperidin-1-yl)benzonitrile (from intermediate D, Example 10) (52 mg, 0.17 mmol) and 4-(trifluoromethyl)benzyl carbonochloridate (71.3 mg, 0.21 mmol) according to General Procedure H to give 27.4 mg (32.2%) of white solid. Anal. Calcd. for C22H31F3N4O2 m/z 500.2, found: 501.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.60 (d, J=8.1 Hz, 2H), 7.48 (m, 4H), 6.98 (d, J=9 Hz, 2H), 5.08 (s, 2H), 3.66 (m, 4H), 3.58 (m, 1H), 3.0 (m, 1H), 2.75 (m, 2H), 2.5 (m, 1H), 2.1 (d, 1H), 2.04 (s, 1H), 1.93 (s, 2H), 1.8 (m, 3H), 1.76 (s, 3H), 1.6 (m, 1H), 1.34 (m, 5H).

Provenance & Evidence