N-{3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1E)-3-methoxyprop-1-en-1-yl]benzyl}cyclopropanamine → N-[3-{[tert-Butyl(dimethyl)silyl]oxy}-5-(3-methoxypropyl)benzyl]cyclo-propanamine
Reaktionsgleichung
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[C:18](/[CH:20]=[CH:21]/[CH2:22][O:23][CH3:24])[CH:19]=1)[CH2:12][NH:13][CH:14]1[CH2:16][CH2:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17]=[C:18]([CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH:19]=1)[CH2:12][NH:13][CH:14]1[CH2:16][CH2:15]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a solution of N-{3-{[tert-butyl(dimethyl)silyl]oxy}-5-[(1E)-3-methoxyprop-1-en-1-yl]benzyl}cyclopropanamine from the previous step (1 eq.) in EtOAc (0.04 M) was added 10% palladium on activated carbon (10 mol %). The vessel was evacuated and back filled with hydrogen. The reaction suspension was then stirred under a balloon atmosphere of hydrogen for 1.5 h. The reaction was diluted with DCM and filtered through a bed of celite. The insolubles were further washed with EtOAc and methanol. Concentration of the filtrate in vacuo afforded the title compound amine 1 as a colorless oil.