反应 #44023

反应方程式

lithium borohydride

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

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

lithium borohydride

→

mixture

收率 57.0%

(8-(4-chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol

收率 57.0%

溶剂

THF

反应条件

后处理

1. 1
   其他was consumed
2. 2
   浓缩The reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and Rochelle's salt
3. 3
   workup.ADDITIONwere added
4. 4
   洗涤The aqueous layer was washed with several more portions of EtOAc
5. 5
   干燥dried with Na2SO4
6. 6
   浓缩concentrated
7. 7
   其他to give 2.44 g of crude oil
8. 8
   其他The material was purified by column chromatography

实验过程

Ethyl 8-(4-chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decane-7-carboxylate (110; 2.47 g, 5.92 mmol) and lithium borohydride (4.7 ml, 2.0 M in THF, 9.48 mmol) were added to THF (15 ml). The mixture was stirred for 18 hours under nitrogen at rt which led to only a 25% conversion to the desired alcohol. Solid lithium borohydride was added in equivalent portions and the reaction monitored until the starting ester was consumed. The reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and Rochelle's salt were added. The aqueous layer was washed with several more portions of EtOAc, dried with Na2SO4, and concentrated to give 2.44 g of crude oil. The material was purified by column chromatography using EtOAc/hexanes gradients to yield 1.26 g (57%) of a mixture of cis/trans isomers.

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