(1S)-2-Nitro-1-[3-({3-[(phenylmethyl)oxy]propyl}oxy)phenyl]ethanol → (1S)-2-Amino-1-[3-({3-[(phenylmethyl)oxy]propyl}oxy)phenyl]ethanol
Reaction equation
[N+:1]([CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:8]=1)[OH:6])([O-])=O>C(O)C.[Pd]>[NH2:1][CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH2:15][CH2:16][O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:8]=1)[OH:6]Participants
4
Procedure
The (1S)-2-nitro-1-[3-({3-[(phenylmethyl)oxy]propyl}oxy)phenyl]ethanol in ethanol solution (8 g in 160 mL) was hydrogenated using a Pd (4%)/Pt(1%)/C catalyst (1.6 g). Upon consumption of the starting material and the hydroxylamine intermediate, the reaction product in ethanol was filtered.