反应 #1100281

反应方程式

BINAP

3-tert-butoxycarbonyl-7-chloro-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

benzophenone hydrazone

sodium tert-butoxide

→

title compound

收率 87.0%

3-tert-Butoxycarbonyl-7-chloro-6-(N′-benzhydrylidene-hydrazino)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

收率 87.0%

反应条件

后处理

1. 1
   其他in dry
2. 2
   其他degassed toluene (100 mL) under nitrogen
3. 3
   温度cool to RT
4. 4
   浓缩concentrate
5. 5
   其他purify
6. 6
   洗涤(silica gel chromatography, eluting with 95:5 2-methylpentane:EtOAc)

实验过程

Dissolve 3-tert-butoxycarbonyl-7-chloro-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (4.39 g, 10.2 mmol) in dry, degassed toluene (100 mL) under nitrogen, then add benzophenone hydrazone (2.00 g, 10.2 mmol), sodium tert-butoxide (1.37 g, 14.3 mmol), BINAP (635 mg, 1.02 mmol) and bis(dibenzylideneacetone)palladium (0) (280 mg, 0.306 mmol). Stir at 100° C. for 8 hr, cool to RT, concentrate and purify (silica gel chromatography, eluting with 95:5 2-methylpentane:EtOAc) to give the title compound (4.2 g, 87%).

来源