Реакция #8858

Уравнение реакции

tert-butyldimethylsilyl chloride

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

imidazole

→

title compound

Выход 86.2%

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

Выход 86.2%

Растворители

ether

sodium bicarbonate

DMF

Условия реакции

Обработка

1. 1
   ЭкстракцияThe mixture was extracted twice with ether
2. 2
   ПромывкаThe combined ether layers were washed with brine
3. 3
   Сушкаdried over sodium sulfate
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe residue was purified by flash chromatography
7. 7
   Промывкаeluting with 5% ethyl acetate in hexanes

Методика

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.

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