Bromide ion → HCID 58171626, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of tert-butyl 3-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (2 g, 7.75 mmol) in dry THF (10 mL) was added 1-propynylmagnesinm bromide (30 mL, 15 mmol) under N2 at −78° C. The reaction mixture was stirred at −78° C. for 0.5 h, allowed to warm to rt slowly and stirred for another 10 h. The mixture was quenched with 2 N aq HCl (20 mL) at 0° C. and extracted with EtOAc (50 mL×3). The combined organic layers were washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and concentrated. The residue was purified by preparative TLC (PE/EA=1:1) to afford tert-butyl 3-(but-2-ynoyl)pyrrolidine-1-carboxylate (1.6 g, 86%) as a white oil.

Provenance & Evidence