2-Methylbenzyloxycarbonyl chloride → 2-Methylbenzyl (1R,2R)-2-((S)-1-(4-cyanophenyl)piperidin-3-ylamino)cyclohexylcarbamate

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Reaction Steps

2-Methylbenzyl (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, 0.20 mmol) and 2-methylbenzyl carbonochloridate (63.5 mg, 0.22 mmol) according to General Procedure H to give 25 mg (27.8%) of white solid. Anal. Calcd. for C27H34N4O2 m/z 446.3, found: 447.2 (M+H)+; 1H NMR (400 MHz, CD3OD) δ ppm 7.45 (d, J=8.7 Hz, 2H), 7.26 (d, J=7.3 Hz, 1H), 7.19 (m, 1H), 7.14 (m, 2H), 6.98 (m, 2H), 5.05 (m, 2H), 3.7 (m, 1H), 3.55 (m, 1H), 3.28 (m, 1H), 2.97 (m, 1H), 2.74 (m, 1H), 2.68 (m, 1H), 2.50 (m, 1H), 2.31 (s, 3H), 2.04 (m, 1H), 1.91 (m, 2H), 1.78 (m, 3H), 1.61 (m, 1H), 1.33 (m, 5H), 1.21 (m, 1H).

Provenance & Evidence