Methyl chloroformate → HCID 118492082, compound

Participants

Reaction Steps

To a solution of (1S,8aS)-N-methyl-N-((R)-1-(3-methyl-5-(trifluoromethyl)phenyl)ethyl)-6-oxo-1-o-tolylhexahydropyrrolo[1,2-a]pyrazine-2(1H)-carboxamide (350 mg, 0.74 mmol) in anhydrous THF (20 mL) under N2 atmosphere was added LHMDS (4.43 mL, 1 M in THF, 4.43 mmol) at −60° C. The reaction was stirred for 30 min followed by addition of methyl carbonochloridate (174 mg, 1.85 mmol). After stirring for another 3 h at room temperature. The reaction was quenched with water at 0° C. and then extracted with EtOAc (2×30 mL). The combined organic layers were dried over anhydrous Na2SO4 and then concentrated in high vacuum. The residue was purified by silica gel chromatography (DCM/MeOH=20/1 to 10/1) to give the title compound (200 mg, yield: 46%); m/z (ES+): 590 [M+H]+.

Provenance & Evidence