Methylamine → HCID 89681741, compound

Participants

Reaction Steps

To a solution of (S)-ethyl 2-(3,4-bis(bromomethyl)-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate (0.1356 g, 0.219 mmol) and triethylamine (61 μL, 0.438 mmol) in anhydrous THF (10 mL) at 0° C. was added a 2M solution of methylamine in THF (109 μL, 0.219 mmol). The reaction mixture was stirred for 1 hour, then stirred overnight at room temperature. LC/MS shows some desired product. Reaction mixture was heated at 45° C. for 1.5 hours, then additional 2M solution of methylamine in THF (109 μL, 0.219 mmol) was added. After 1 hour, 2M solution of methylamine in THF (0.9 mL) was added and stirred for 45 minutes. LC/MS showed no starting material. The reaction mixture was concentrated and purified by flash column chromatography (silica gel, 30 to 100% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C22H27F3NO6S: 490.2. Found: 490.1.

Provenance & Evidence