반응 #685022

반응 방정식

1,5-dioxa-9-aza spiro[5.5]undecane

triethylamine

benzyl chloroformate

→

title compound

수율 68.0%

Benzyl 1,5-dioxa-9-azaspiro[5.5]undecane-9-carboxylate

수율 68.0%

용매

EtOAc

THF

THF

반응 조건

후처리

1. 1
   세척the mixture was washed with water and brine
2. 2
   건조dried (Na2SO4)
3. 3
   농축Concentration
4. 4
   기타gave yellow oil that
5. 5
   기타was purified by flash chromatography
6. 6
   세척eluting with 20%-50% EtOAc/hexane

실험 절차

To a solution of 1,5-dioxa-9-aza spiro[5.5]undecane (15.0 g, 95.4 mmol) and triethylamine (17.6 mL, 126 mmol) in THF (140 mL) cooled to 0° C. was added dropwise a solution of benzyl chloroformate (14 mL, 97.5 mmol) dissolved in THF (30 mL). The resulting mixture was stirred at room temp for 18 h. After diluting with EtOAc, the mixture was washed with water and brine and dried (Na2SO4). Concentration gave yellow oil that was purified by flash chromatography eluting with 20%-50% EtOAc/hexane to give the title compound as colorless oil (18.9 g, 68% yield). 1H NMR (300 MHz, CDCl3) δ: 7.36-7.27 (5H, m), 5.09 (2H, s), 3.89-3.85 (4H, m), 3.51-3.47 (4H, m), 1.87-1.66 (6H, m). LCMS (M+H) calcd for C16H22NO4: 292.15; found: 292.00.

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