تفاعل #685022

معادلة التفاعل

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

triethylamine

benzyl chloroformate

→

title compound

المردود 68.0%

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

المردود 68.0%

المذيبات

EtOAc

THF

THF

ظروف التفاعل

المعالجة

1. 1
   غسيلthe mixture was washed with water and brine
2. 2
   تجفيفdried (Na2SO4)
3. 3
   تركيزConcentration
4. 4
   أخرىgave yellow oil that
5. 5
   أخرىwas purified by flash chromatography
6. 6
   غسيلeluting with 20%-50% EtOAc/hexane

الإجراء التجريبي

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.

المصدر