반응 #8858

반응 방정식

tert-butyldimethylsilyl chloride

tert-butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

imidazole

→

title compound

수율 86.2%

tert-Butyl 1-vinyl-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate

수율 86.2%

용매

ether

sodium bicarbonate

DMF

반응 조건

후처리

1. 1
   추출The mixture was extracted twice with ether
2. 2
   세척The combined ether layers were washed with brine
3. 3
   건조dried over sodium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated
6. 6
   기타The residue was purified by flash chromatography
7. 7
   세척eluting with 5% ethyl acetate in hexanes

실험 절차

To a solution of tert-butyl 1-vinyl-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (0.462 g, 1.64 mmoL) from Step A in DMF (8 mL) was added imidazole (0.335 mg, 4.92 mmol) and then tert-butyldimethylsilyl chloride (0.370 g, 2.4 mmol). The reaction was stirred at room temperature for 20 h and then diluted with ether and sodium bicarbonate solution. The mixture was extracted twice with ether. The combined ether layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 5% ethyl acetate in hexanes to afford the title compound (0.56 g) as a mixture of isomers.

출처