HCID 86657052, compound → tert-Butyl 2-(prop-2-yn-1-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Into a 3,000 ml 3-necked roundbottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of tert-butyl 2-(3,3-dibromoprop-2-en-1-yl)pyrrolidine-1-carboxylate (103 g, 279 mmol) in tetrahydrofuran (1,000 ml). The solution was cooled to −80° C. and n-butyl lithium (231 mL, 2.00 equiv, 155 g/L) was added dropwise such that the internal temperature was maintained at −80° C. (180 minute addition time). The resulting solution was allowed to warm to ambient temperature and then allowed to stir for 1 h. The reaction mixture was quenched by the addition of 500 mL of water. The resulting solution was extracted three times with 500 mL of diethyl ether and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography (ethylacetate/petroleum ether gradient) to afford tert-butyl 2-prop-2-yn-1-ylpyrrolidine-1-carboxylate.

Provenance & Evidence