تفاعل #568256

معادلة التفاعل

4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta(b)pyrrole-3-carboxylic acid ethyl ester

3-amino-prop-2-enal

ammonium acetate

→

3,4,5,6-tetrahydro-3,10-diaza-benzo[e]azulene-1-carboxylic acid ethyl ester

المردود 20.0%

المذيبات

NaHCO3

triethylamine

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةIt is cooled to room temperature
2. 2
   أخرىLayers are separated
3. 3
   استخلاصthe aqueous phase is extracted with 4:1 DCM/2-propanol (4×100 mL)
4. 4
   تجفيفCombined organic layers are dried (Na2SO4)
5. 5
   أخرىevaporated
6. 6
   غسيلFlash Chromatography on silica gel, eluting with EtOAc:triethylamine (20:1)

الإجراء التجريبي

A mixture of 4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta(b)pyrrole-3-carboxylic acid ethyl ester (7.0 g, 31.67 mmol), 3-amino-prop-2-enal (3.37 g, 47.5 mmol) and ammonium acetate (365 mg, 4.75 mmol) in triethylamine (7 mL) is heated at 110° C. for 4 h. It is cooled to room temperature and the solid residue is dissolved in 100 mL dichloromethane and 100 mL sat. NaHCO3 solution. Layers are separated and the aqueous phase is extracted with 4:1 DCM/2-propanol (4×100 mL). Combined organic layers are dried (Na2SO4) and evaporated. Flash Chromatography on silica gel, eluting with EtOAc:triethylamine (20:1), provides 3,4,5,6-tetrahydro-3,10-diaza-benzo[e]azulene-1-carboxylic acid ethyl ester (1.6 g, 20%) as off-white solid. 1H NMR (400 MHz, CD3OD) δ1.247 (3H, t), 2.227 (2H, m), 2.631 (4H, m), 4.197 (2H, q), 7.170 (1H, m), 7.405 (1H, s), 7.686 (1H, d), 8.375 (1H, d). MS (ES+) 257 (M+1)

المصدر