Trifluoroacetic acid → 1-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidine

反応式

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](O)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

実験手順

A solution of 1-benzyloxycarbonyl-4-hydroxy-4-(2-methylthiophenyl)piperidine (2.89 g) in dichloromethane (80 mL) was treated with 6.2 mL of trifluoroacetic acid followed by 25.7 mL of triethylsilane and stirred for 16 hours. At the end of this period, the volatile material was distilled under reduced pressure and the resulting residue was chromatographed. Elution with 3:1 hexane:ethyl acetate afforded the named material (2.02 g); MS: 342(M+1); NMR: 1.5-1.6 (br, 2), 1.8-1.9 (m, 2), 2.45 (s, 3), 2.8-2.9 (m, 2), 3.1-3.2 (m, 1), 4.3 (br, 2), 5.1 (s, 2), 7.1-7.2 (m, 2), 7.2-7.3 (m, 2), 7.3-7.4 (m, 5).