Reacción #53851

Ecuación de reacción

Water

trans-[4-(2-Hydroxy-ethylsulfanylmethyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester

methanesulfonylchloride

pyridine

→

trans-[4-(2-Chloro-ethylsulfanylmethyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester

Rendimiento 104.7%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónAfter extraction with aqueous 10% KHSO4/Et2O (3×)
2. 2
   Lavadothe organic phases were washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl
3. 3
   Secadodried over Na2SO4
4. 4
   Otroevaporated

Procedimiento

A solution of 645 mg (corresponds to 1.65 mmol) of trans-[4-(2-Hydroxy-ethylsulfanylmethyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester in 12 ml CH2Cl2 was treated at 0° C. with 0.14 ml (1.82 mmol) methanesulfonylchloride, 0.20 ml (2.45 mmol) pyridine and 202 mg (1.65 mmol) DMAP. The reaction mixture was warmed up over night to room temperature. Water (2 ml) was added and the reaction was stirred for 5 min. After extraction with aqueous 10% KHSO4/Et2O (3×), the organic phases were washed with aqueous saturated NaHCO3 (2×), aqueous 10% NaCl, dried over Na2SO4 and evaporated to yield 650 mg (quantitative) trans-[4-(2-Chloro-ethylsulfanylmethyl)-cyclohexyl]-methyl-carbamic acid 4-chloro-phenyl ester, MS: 376 (MH+, 2Cl).

Fuente