Реакция #8849

Уравнение реакции

HCl

tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate

ethyl formate

potassium t-butoxide

→

title compound

Выход 51.4%

tert-Butyl 2-(hydroxymethyl)-1-oxo-8-azaspiro[4.5]decane-8-carboxylate

Выход 51.4%

Растворители

diethyl ether

Условия реакции

Обработка

1. 1
   Другоеby evaporating with toluene (10 mL) three times in vacuo
2. 2
   workup.DISSOLUTIONdissolved in methyl-tert-butyl ether (5 mL)
3. 3
   Экстракцияextracted three times with diethyl ether
4. 4
   Промывкаwashed with brine
5. 5
   Сушкаdried over sodium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   Другоеto afford 0.575 g
9. 9
   ДругоеThe residue was purified by flash chromatography
10. 10
    Промывкаeluting with 45% ethyl acetate/hexanes

Методика

tert-Butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate from Procedure 1, Step G (0.526 g, 2.08 mmol) was dried by evaporating with toluene (10 mL) three times in vacuo, dissolved in methyl-tert-butyl ether (5 mL), and cooled to −78° C. To this solution was added ethyl formate (0.336 mL, 4.15 mmol) and then potassium t-butoxide (0.466 g, 4.16 mmol). After 2 days, the reaction mixture was diluted with diethyl ether, poured into 2N HCl, and extracted three times with diethyl ether. The organic layers were combined, washed with brine, dried over sodium sulfate, filtered, and concentrated to afford 0.575 g. The residue was purified by flash chromatography eluting with 45% ethyl acetate/hexanes to give the title compound (0.303 g). MS/EI (acetonitrile/water): m/z 304 (M+1+Na) retention time=2.9 min.

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