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

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Reaction Steps

2-Chlorobenzyl (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) (60 mg, 0.2 mmol) and 2-chlorobenzyl carbonochloridate (68 mg, 0.22 mmol) according to General Procedure H to give 20 mg (21.3%) of pale yellow solid. Anal. Calcd. for C26H31ClN4O2 m/z 466.2, found: 467.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.44 (d, J=8.7 Hz, 2H), 7.38 (m, 2H), 7.29 (m, 2H), 6.98 (d, J=9 Hz, 2H), 5.1 (s, 2H), 3.69 (m, 1H), 3.56 (m, 1H), 3.29 (m, 1H), 3.02 (m, 1H), 2.79 (d, J=8.4 Hz, 2H), 2.54 (m, 1H), 2.05 (m, 1H), 1.92 (m, 2H), 1.79 (m, 3H), 1.64 (m, 1H), 1.34 (m, 5H), 1.22 (m, 1H).

Provenance & Evidence