1-Benzyloxycarbonyl-4-hydroxy-4-(4-trifluoromethylphenyl)-piperidine → 4-[4-(Trifluoromethyl)phenyl]piperidin-4-ol

反応式

C(OC([N:11]1[CH2:16][CH2:15][C:14]([OH:27])([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:27][C:14]1([C:17]2[CH:18]=[CH:19][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:21][CH:22]=2)[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1

参加物

実験手順

A mixture of 1-benzyloxycarbonyl-4-hydroxy-4-(4-trifluoromethylphenyl)-piperidine (12.3 g, 32.4 mmol), ethanol (150 mL), and 10% palladium on carbon (1.4 g) was hydrogenated in a Parr apparatus (initial hydrogen pressure was 48 psi). After 2.5 hours, the mixture was filtered through celite and concentrated. The residue was triturated with ether/hexane to obtain 4.98 g (63%) of 4-hydroxy-4-(4-trifluoromethylphenyl)-piperidine as a white solid which had mp 130.5°-132° C. Analysis calculated for C12 H14F3NO--0.25 H2O: C, 57.71; H, 5.85; N, 5.61. Found: C, 57.91; H 5.77; N, 5.54.