4-(Aminomethyl)benzonitrile → tert-butyl (2S,3R)-4-(4-cyanobenzylamino)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate
Reaction equation
[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]2[CH2:11][O:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)#[N:21]>CC#N>[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:27][CH2:11][C@@H:9]([OH:10])[C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:24][CH:23]=1)#[N:21]Participants
4
Procedure
To a solution of tert-butyl (S)-2-cyclohexyl-1-((S)-oxiran-2-yl)ethylcarbamate (67.3 mg, 0.25 mmol) in CH3CN (8 mL) was added 4-cyanobenzylamine (39.6 mg, 0.3 mmol) and the mixture was heated under reflux overnight. The solvent was removed in vacuo and the residue was purified by the preparative HPLC to give tert-butyl (2S,3R)-4-(4-cyanobenzylamino)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (58 mg, 58%). 1H NMR: 0.82 (m, 1H), 0.95 (m, 1H), 1.10-1.48 (m, 5H), 1.45 (s, 9H), 1.55-1.68 (m, 5H), 1.76 (m, 1H), 2.65 (m, 2H), 3.46 (m, 1H), 3.85 (m, 2H), 4.49 (m, 1H), 7.42 (d, 2H), 7.59 (d, 2H). MS (E/Z): 402 (M+H+).