1-Chloroethyl chloroformate → HCID 69217200, compound

Participants

Reaction Steps

2-[5-(3-Isopropoxyphenyl)-2,4-dimethyl-2-aza-bicyclo[3 .3.1 ]non-7-yl]-isoindole-1,3-dione (2.5) (1.50 g, 3.5 mmol) was dissolved in dichloroethane and heated to reflux followed by the addition of 1-chloroethyl chloroformate (0.410 ml, 3.8 mmol). This solution was allowed to reflux for 3.5 hrs. The reaction was cooled and the solvent removed under reduced pressure. The crude material was taken up in ethyl acetate and washed with a saturated sodium bicarbonate solution (3×30 ml). The organic layer was collected, dried (Na2SO4) and the solvent removed under reduced pressure yielding crude product. This material was dissolved in methanol and refluxed overnight. The methanol was removed and the crude product dissolved in 1 N NaOH. The aqueous was extracted with 3:1 CH2Cl2:THF. The combined organic layers were collected, dried (Na2SO4) and the solvent removed under reduced pressure yielding crude product. This product was used with out further purification.

Provenance & Evidence