Hydrogen Bromide → (9H-fluoren-9-yl)methyl 4-(bromoacetyl)piperidine-1-carboxylate

反応式

[N+](=[CH:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH:16]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH2:8][CH2:7]1)=[O:5])=[N-].[BrH:29]>C1COCC1.O>[Br:29][CH2:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][CH:16]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH2:8][CH2:7]1)=[O:5]

参加物

実験手順

A solution of (9H-fluoren-9-yl)methyl 4-(diazoacetyl)piperidine-1-carboxylate (5 g, 13.3 mmol) in THF was cooled in an ice water bath and was treated with an aqueous HBr solution (10 mL). This reaction mixture was stirred at RT for 2 h. The reaction mixture was diluted with water and the organic content was extracted using EtOAc, dried over Na2SO4, filtered and concentrated at reduced pressure. The crude product was chromatographed over silica gel eluting with a gradient (0-15% EtOAc:hexanes) to afford (9H-fluoren-9-yl)methyl 4-(bromoacetyl)piperidine-1-carboxylate (3 g, 53%) as an off white solid.