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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

수율 73.0%

용매

dioxane

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후처리

1. 1
   추출extracted with EtOAc/1N HCl and water
2. 2
   농축The organic phases were concentrated under reduced pressure
3. 3
   기타purified by chromatography on silica gel with EtOAc/hexane 1:3

실험 절차

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).

출처