반응 #8849

반응 방정식

HCl

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

ethyl formate

potassium t-butoxide

→

title compound

수율 51.4%

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

수율 51.4%

용매

diethyl ether

반응 조건

후처리

1. 1
   기타by evaporating with toluene (10 mL) three times in vacuo
2. 2
   workup.DISSOLUTIONdissolved in methyl-tert-butyl ether (5 mL)
3. 3
   추출extracted three times with diethyl ether
4. 4
   세척washed with brine
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타to afford 0.575 g
9. 9
   기타The residue was purified by flash chromatography
10. 10
    세척eluting with 45% ethyl acetate/hexanes

실험 절차

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.

출처