N-((1R)-1-benzyl-2-(benzylamino)ethyl)-N-methylcarbamic acid tert-butylester → N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester
Reaktionsgleichung
[C:1]([O:5][C:6](=[O:26])[N:7]([C@H:9]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:10][NH:11]CC1C=CC=CC=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]>[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:26])[N:7]([C@@H:9]([CH2:10][NH2:11])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:8])([CH3:2])([CH3:4])[CH3:3]Komponenten
3
Versuchsvorschrift
A suspension of 20% palladium hydroxide on charcoal (4.63 g) and N-((1R)-1-benzyl-2-(benzylamino)ethyl)-N-methylcarbamic acid tert-butylester (4.40 g, 12.4 mmol) was kept for 8 h under a hydrogen atmosphere at (pressure: 1 atm). The reaction mixture was flushed with nitrogen and filtered through a plug of celite. The solvent was removed. The crude product was purified by flash chromatography on silica (110 g), using dichloromethane/methanol/25% aqueous ammonia as eluent, to give 830 mg of N-((1R)-1-aminomethyl-2-phenylethyl)-N-methylcarbamic acid tert-butylester.