2,3-dihydro-1H-pyrrolizine → HCID 13478513, compound

Participants

Reaction Steps

To a stirred, ice-cooled mixture of 2,3-dihydro-1H-pyrrolizine (0.40 g, 0.0037 m), methyl 5-(chlorocarbonyl)-1,4-dimethylpyrrole-2-acetate (1.1 g, 0.0037 m), and methylene chloride (10 ml) was added dropwise over 3 minutes stannic chloride (0.86 ml, 0.0075 m), and the resulting mixture allowed to stir cold for ca. 30 minutes. The mixture was partitioned between ether and water, and the ether layer washed and dried. It was concentrated in vacuo to a yellow residue which was then eluted on a silica gel chromatograph column with 30% ethyl acetate/hexane to yield 0.35 g of methyl 1,4-dimethyl-5-(2,3-dihydro-1H-pyrrolizin-5-oyl)pyrrole-2-acetate.

Provenance & Evidence