反应 #53874

反应方程式

trans-Methansulfonic acid 5-(4-methyl amino-cyclohexyl)-pentyl ester

trifluoroacetic acid

4-chlorophenyl chloroformate

Hünig's base

→

trans-Methanesulfonic acid 5-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-pentyl ester

收率 73.0%

溶剂

dioxane

反应条件

后处理

1. 1
   萃取extracted with EtOAc/1N HCl and water
2. 2
   浓缩The organic phases were concentrated under reduced pressure
3. 3
   其他purified by chromatography on silica gel with EtOAc/hexane 1:3

实验过程

To a solution of 245 mg (0.53 mmol) trans-Methansulfonic acid 5-(4-methyl amino-cyclohexyl)-pentyl ester.trifluoroacetic acid salt and 143.5 mg (0.75 mmol) 4-chlorophenyl chloroformate in 4 ml dioxane, was added at RT 1.54 ml (3.12 mmol) Hünig's base. The mixture was stirred for 1 h, then extracted with EtOAc/1N HCl and water. The organic phases were concentrated under reduced pressure and purified by chromatography on silica gel with EtOAc/hexane 1:3 to yield 167 mg (73%, 2 steps) of pure trans-Methanesulfonic acid 5-{4-[(4-chloro-phenoxycarbonyl)-methyl-amino]-cyclohexyl}-pentyl ester, MS: 432 (MH+, 1Cl).

来源