反应 #44022

反应方程式

Ethyl 1-(4-chlorophenylsulfonyl)-6-ethyl-4-oxopiperidine-2-carboxylate

ethyl 1-(4-chlorophenylsulfonyl)-6-ethyl-4-oxopiperidine-2-carboxylate

TMSCl

ethylene glycol

→

mixture

收率 96.0%

ethyl 8-(4-chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decane-7-carboxylate

收率 96.0%

溶剂

CH2Cl2

反应条件

后处理

1. 1
   温度refluxed under nitrogen for 3 hours
2. 2
   浓缩The reaction mixture was concentrated tinder reduced pressure
3. 3
   洗涤The aqueous layer was washed with several more portions of EtOAc
4. 4
   干燥dried over Na2SO4
5. 5
   浓缩concentrated

实验过程

Ethyl 1-(4-chlorophenylsulfonyl)-6-ethyl-4-oxopiperidine-2-carboxylate (109; 5.31 g, 14.2 mmol), TMSCl (5.41 ml, 42.6 mmol), and ethylene glycol (3.96 ml, 71.0 mmol) were added to CH2Cl2 (50 ml) and refluxed under nitrogen for 3 hours. The reaction mixture was concentrated tinder reduced pressure, and taken up in equal portions of EtOAc and water. The aqueous layer was washed with several more portions of EtOAc, dried over Na2SO4, and concentrated to give 5.67 g (96%) of a mixture of cis/trans (4:96) isomers as a clear oil which solidified upon standing. The material was used without further purification.

来源