Ammonium Chloride → (S)-t-Butyl 2-(4-(3,4-dimethoxyphenoxy)-3-oxobut-1-yn-1-yl)pyrrolidine-1-carboxylate

Participants

Reaction Steps

To a THF (120 mL) solution of (S)-t-butyl 2-(2,2-dibromovinyl)pyrrolidine-1-carboxylate (5.326 g), n-BuLi (11.6 mL, 2.64 N hexane solution) was added dropwise at −78° C. and the mixture was stirred at the same temperature for an hour; thereafter, a THF (50 mL) solution of the compound (4.00 g) obtained in Example 14-(1) was added dropwise and temperature was raised to room temperature over an hour. The reaction mixture was added to a saturated aqueous solution of NH4Cl (400 mL) and the organic layer extracted with AcOEt (400 mL×2) was dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (2.934 g, pale yellow oil.)

Provenance & Evidence