(4-methylphenyl)methyl carbonochloridate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-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, 0.2 mmol) and 4-methylbenzyl carbonochloridate (63.5 mg, 0.22 mmol) according to General Procedure H to give 20 mg (22.3%) 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), 7.19 (d, J=7.6 Hz, 2H), 7.11 (d, J=7.6 Hz, 2H), 6.96 (d, J=3 Hz, 2H), 4.98 (m, 2H), 3.68 (dm, 1H), 3.28 (m, 1H), 2.97 (m, 1H), 2.70 (m, 1H), 2.50 (m, 1H), 2.31 (s, 3H), 2.04 (m, 1H), 1.92 (m, 2H), 1.78 (m, 3H), 1.62 (m, 1H), 1.30 (m, 6H).

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-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, 0.2 mmol) and 4-methylbenzyl carbonochloridate (63.5 mg, 0.22 mmol) according to General Procedure H to give 20 mg (22.3%) 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), 7.19 (d, J=7.6 Hz, 2H), 7.11 (d, J=7.6 Hz, 2H), 6.96 (d, J=3 Hz, 2H), 4.98 (m, 2H), 3.68 (dm, 1H), 3.28 (m, 1H), 2.97 (m, 1H), 2.70 (m, 1H), 2.50 (m, 1H), 2.31 (s, 3H), 2.04 (m, 1H), 1.92 (m, 2H), 1.78 (m, 3H), 1.62 (m, 1H), 1.30 (m, 6H).