tert-butyl (1S,2R)-1-benzyl-3-[(cyclohexyloxy)amino)-2-hydroxypropylcarbamate → (2R,3S)-3-amino-1-[(cyclohexyloxy)amino]-4-phenyl-2-butanol
Reaction equation
[CH2:1]([C@H:8]([NH:20]C(=O)OC(C)(C)C)[C@H:9]([OH:19])[CH2:10][NH:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[NH2:20][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]([OH:19])[CH2:10][NH:11][O:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1Participants
3
Procedure
A combination of trifluoroacetic acid (20 mL) and tert-butyl (1S,2R)-1-benzyl-3-[(cyclohexyloxy)amino]-2-hydroxypropylcarbamate (2.00 g, 5.29 mmol) was stirred under Argon at ambient temperature for approximately 30 minutes. The reaction was evaporated in vacuo and the residue was partitioned between dichloromethane and aqueous sodium hydroxide (1N). After separating the layers, the aqueous phase was extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a solid which was dried under high vacuum to provide (2R,3S)-3-amino-1-[(cyclohexyloxy)amino]-4-phenyl-2-butanol (1.426 g, 97%). H1-NMR (chloroform-D3): 1.24 (m, 5H), 1.58 (m, 4H), 1.73 (m, 2H), 1.95 (m, 2H), 2.51 (m, 1H), 2.97 (m, 2H), 3.16 (m, 2H), 3.33 (m, 1H), 3.57 (m, 1H), 3.77 (m, 1H), 7.26 (m, 5H). MS(ESI): 279(M+H).