Trifluoroacetic acid → (S,Z)-3-amino-1-benzyl-3,4,7,8-tetrahydroazocin-2(1H)-one
Reaction equation
[CH2:1]([N:8]1[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][C@H:10]([NH:16]C(=O)OC(C)(C)C)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:16][C@H:10]1[CH2:11][CH:12]=[CH:13][CH2:14][CH2:15][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:24]Participants
4
Procedure
To a solution of (S,Z)-tert-butyl 1-benzyl-2-oxo-1,2,3,4,7,8-hexahydroazocin-3-ylcarbamate (10 mg, 0.030 mmol) in DCM (0.2 mL) at rt was added TFA (0.2 mL). The clear solution was stirred at rt for 40 min. The reaction mixture was concentrated and dried in vacuum to give (S,Z)-3-amino-1-benzyl-3,4,7,8-tetrahydroazocin-2(1H)-one (7.0 mg, 0.030 mmol, 100% yield) as an oil. Anal. Calcd. for C14H18N2O m/z 230.3. found: 231.1 (M+H)+.