反応 #53844

反応方程式

trans-(4-Methylamino-cyclohexyl)-methanol

4-chlorophenylchloroformate

H2O

→

trans-(4-Hydroxymethyl-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester

溶媒

hexamethyldisilazane

反応条件

後処理

1. 1
   温度refluxed for 5 h
2. 2
   その他The solution was evaporated under reduced pressure
3. 3
   workup.DISSOLUTIONdissolved in 50 ml THF
4. 4
   その他were evaporated
5. 5
   抽出The residue was extracted with water/Et2O (3×)
6. 6
   洗浄the organic phases were washed with 10% NaCl
7. 7
   乾燥dried over Na2SO4
8. 8
   その他evaporated

実験手順

4.60 g (32.14 mmol) of trans-(4-Methylamino-cyclohexyl)-methanol was suspended in 85 ml hexamethyldisilazane and refluxed for 5 h. The solution was evaporated under reduced pressure and dissolved in 50 ml THF. 6.14 g (32.14 mmol) of 4-chlorophenylchloroformate were added slowly at 0° C. and stirred for 16 h at room temperature. 30 ml H2O were added and after 1 h the solvents were evaporated. The residue was extracted with water/Et2O (3×), the organic phases were washed with 10% NaCl, dried over Na2SO4 and evaporated to yield after flash-chromatography on silica gel (hexane/EtOAc 4:1 to 1:1) 5.48 g (57%) of trans-(4-Hydroxymethyl-cyclohexyl)-methyl-carbamic acid 4-chloro-phenyl ester, MS: 298 (MH+, 1Cl).

出典