Boron tribromide → (+/-)-trans-2-Diethylaminocarbonyl-3,7-dimethyl-4a-(3-hydroxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinoline
反応式
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4]([C:6]1[NH:18][C:17]2[CH2:16][C@@H:15]3[C@:10]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=4)([CH2:11][CH2:12][N:13]([CH3:19])[CH2:14]3)[CH2:9][C:8]=2[C:7]=1[CH3:28])=[O:5])[CH3:2].B(Br)(Br)Br>>[CH2:29]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[NH:18][C:17]2[CH2:16][C@@H:15]3[C@:10]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=4)([CH2:11][CH2:12][N:13]([CH3:19])[CH2:14]3)[CH2:9][C:8]=2[C:7]=1[CH3:28])=[O:5])[CH3:30]参加物
3
反応物 2
生成物 1
実験手順
0.29 g (0.71 mmol) of (±)-trans-2-diethylaminocarbonyl-3,7-dimethyl-4a-(3-methoxyphenyl)-4,4a,5,6,7,8,8a,9-octahydro-1H-pyrrolo[3,2-g]isoquinoline were treated with 0.4 ml (4.26 mmol) of boron tribromide as described in example 2. The residue was purified by flash chromatography (CH2Cl2 /MeOH/conc. NH4OH 80:12:0.8). The crude product was triturated with a mixture of acetone/MeOH=3:2, yielding 0.14 g of the title compound. M.p.=235°-238 l ° C.