Реакция #8860

Уравнение реакции

tert-butyl 1-(1-hydroxyprop-1-yl)-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate

tetrabutylammonium fluoride

→

title compound

Выход 99.0%

tert-Butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

Выход 99.0%

Растворители

ethyl acetate

HCl

THF

THF

Условия реакции

Обработка

1. 1
   Экстракцияextracted twice with ethyl acetate
2. 2
   ПромывкаThe combined organic 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 50% ethyl acetate in hexanes

Методика

To a solution of tert-butyl 1-(1-hydroxyprop-1-yl)-2-(tert-butyldimethylsilyloxy)-8-azaspiro[4.5]decane-8-carboxylate (0.248 g, 0.58 mmol) in THF (15 mL) was added 1M tetrabutylammonium fluoride in THF (2.3 mL, 2.3 mmol). The solution was stirred at room temperature for 4 h and was then diluted with ethyl acetate, poured into IN HCl, and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 50% ethyl acetate in hexanes to afford the title compound (0.18 g) as a mixture of isomers.

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