Ammonium Chloride → Tert-butyl N-[1-(prop-2-ynoyl)cyclopropyl]carbamate

Participants

Reaction Steps

To a stirred solution of tert-butyl 1-(methoxy(methyl)carbamoyl)cyclopropylcarbamate (5.0 g, 20.49 mmol, 1.0 eq) in THF at −78° C. was added (trimethylsilyl)acetylene (6.36 g, 61.15 mmol, 3.0 eq), and the stirring continued at the same temperature for 5 hr. Product formation was confirmed by LCMS. Saturated NH4Cl solution was added to the reaction mixture, which was then extracted with EtOAC. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography using silica gel (60-120). The desired compound was eluted with 15% EtOAC in Pet ether. Yield: 1.5 g (35.70%).

Provenance & Evidence