Ammonium Chloride → HCID 86706763, compound

Participants

Reaction Steps

To a THF (50 mL) solution of 1,2-dimethoxy-4-(prop-2-yn-yloxy)benzene (2.118 g), n-BuLi (4.0 mL, 2.64 N hexane solution) was added dropwise at −78° C. and the resulting mixture was stirred at the same temperature for 30 minutes; the reaction mixture was then added dropwise to a solution of (S)-t-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (2.578 g) in THF (100 mL) at −78° C. and, after stirring at the same temperature for an hour, temperature was raised to room temperature over an hour. The reaction mixture was added to a saturated aqueous solution of NH4Cl (300 mL) to separate the organic layer, which was washed with a saturated aqueous solution of NH4Cl (100 mL), dried (Na2SO4), filtered and concentrated to give a crude product, which was further purified by neutral silica gel chromatography (AcOEt/hexane) to give the titled compound (2.479 g, pale brown oil.)

Provenance & Evidence