Reacción #220003

Ecuación de reacción

chloroiodomethane

2,3-dihydro-pyrrole-1-carboxylic acid benzyl ester

2,3-Dihydro-pyrrole-1-carboxylic acid benzyl ester

diethylzinc

→

desired product

Rendimiento 50.0%

2-Aza-bicyclo[3.1.0]hexane-2-carboxylic acid benzyl ester

Rendimiento 50.0%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm up to room temperature
2. 2
   workup.STIRRINGstirred an additional 3 h
3. 3
   OtroThe reaction mixture was partitioned between an aqueous solution of ammonium chloride and diethyl ether
4. 4
   ExtracciónThe aqueous layer was extracted with diethyl ether
5. 5
   Lavadothe combined organic layers were washed with brine
6. 6
   Secadodried over sodium sulphate
7. 7
   Otroevaporated in vacuo
8. 8
   Otropurified on silica
9. 9
   Lavadoeluting with a 1:1 to 1:3 gradient of cyclohexane/dichloromethane

Procedimiento

To a cold (0° C.) solution of 2,3-dihydro-pyrrole-1-carboxylic acid benzyl ester (example 4, step 5, 300 mg, 1.0 eq.) in diethyl ether was slowly added a solution of diethylzinc in hexanes (1M, 7 mL, 4.75 eq.), followed by chloroiodomethane (1.1 mL, 10 eq.). The reaction mixture was stirred 3 h at 0° C., allowed to warm up to room temperature and stirred an additional 3 h. The reaction mixture was partitioned between an aqueous solution of ammonium chloride and diethyl ether. The aqueous layer was extracted with diethyl ether and the combined organic layers were washed with brine, dried over sodium sulphate and evaporated in vacuo and purified on silica, eluting with a 1:1 to 1:3 gradient of cyclohexane/dichloromethane, to yield 160 mg (50%) of the desired product as colourless oil. MS (m/e): 218.5 (MH+, 100%)

Fuente