Reaktion #220003

Reaktionsgleichung

chloroiodomethane

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

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

diethylzinc

→

desired product

Ausbeute 50.0%

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

Ausbeute 50.0%

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm up to room temperature
2. 2
   workup.STIRRINGstirred an additional 3 h
3. 3
   SonstigeThe reaction mixture was partitioned between an aqueous solution of ammonium chloride and diethyl ether
4. 4
   ExtraktionThe aqueous layer was extracted with diethyl ether
5. 5
   Waschenthe combined organic layers were washed with brine
6. 6
   Trocknendried over sodium sulphate
7. 7
   Sonstigeevaporated in vacuo
8. 8
   Sonstigepurified on silica
9. 9
   Wascheneluting with a 1:1 to 1:3 gradient of cyclohexane/dichloromethane

Vorschrift

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%)

Quelle