반응 #435722

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(+/−)-trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-one

1,4-dioxa-8-azaspiro[4,5]decane

cyclohexene oxide

→

(+/−)-trans-2-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-cyclohexanol

수율 91.0%

용매

ethanol

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후처리

1. 1
   온도The reaction mixture was refluxed for 40 hours
2. 2
   농축concentrated
3. 3
   기타The residue was chromatographed over silica gel (hexane/ethylacetate 4:1)

실험 절차

Preparation of (+/−)-trans-1-(2-hydroxy-cyclohexyl)-piperidin-4-one. To a solution of 1,4-dioxa-8-azaspiro[4,5]decane (14.7 g, 100 mmol) in ethanol (75 ml) was added cyclohexene oxide (10.0 g, 100 mmol). The reaction mixture was refluxed for 40 hours then cooled to room temperature and concentrated. The residue was chromatographed over silica gel (hexane/ethylacetate 4:1) to provide (+/−)-trans-2-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-cyclohexanol (22.1 g, 91%) as a white solid, MS (ISP): m/e=241.2 (M+).

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