{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-phenyl}-carbamic acid benzyl ester → 4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-phenylamine
Reaktionsgleichung
C(OC(=O)[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:22][CH2:21][CH:20]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:19][CH:18]=2)=[CH:13][CH:12]=1)C1C=CC=CC=1>CCOC(C)=O>[C:27]([Si:24]([CH3:26])([CH3:25])[O:23][CH:20]1[CH2:19][CH2:18][CH:17]([C:14]2[CH:13]=[CH:12][C:11]([NH2:10])=[CH:16][CH:15]=2)[CH2:22][CH2:21]1)([CH3:30])([CH3:29])[CH3:28]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-phenyl}-carbamic acid benzyl ester (Intermediate 16) (350 mg, 0.8 mmol) was dissolved in EtOAc (35 mL). After de-gas by vacuum/nitrogen exchange, Pd—C (70 mg) was added. The reaction mixture was first purged with nitrogen and then hydrogen introduced by vacuum/hydrogen purge cycle. The reaction mixture was stirred at rt overnight when TLC (30% EtOAc in heptane, UV) could not detect the starting material. The reaction mixture was filtered through a celite pad, rinsed with EtOAc. The filtrate was concentrated in vacuo. The residue was purified on a silica gel column, eluted with 10-20% EtOAc in heptane to obtain the title compound as an oil which solidified on standing 130 mg (0.42 mmol, 53% yield).