Dimethylamine → HCID 12992938, compound

Participants

Reaction Conditions

Reaction Steps

To a 125 mL Erlenmeyer flask equipped with a stir bar and a screw cap was added compound (ii), above, (1.48 g; 6.17 mmol) and THF (15 mL). The solution was cooled to 0° C. and triethylamine (5.16 mL; 37 mmol) and methane sulfonyl chloride (0.53 mL; 6.79 mmol) added. The reaction mixture was stirred at 0° C. for 2 h. At this point dimethylamine (2M in tetrahydrofuran)(30.8 mL; 61.7 mmol) was added and the reaction mixture heated to 70° C. for 14 h. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate (50 mL) and the organic phase successively washed with water (3×30 mL), brine (30 mL), dried (sodium sulfate), filtered and the solvent removed in vacuo. The crude residue was purified by column chromatography on silica gel using dichloromethane:ammonia/methanol (2N) (99:1) to yield the title compound as a brown oil (1.2 g; 73%). 13C NMR (CDCl3): δ 136.8, 128.7, 127.4, 122.6, 122.2, 115.1, 122.3, 101.6, 58.9, 45.8, and 44.8.

Provenance & Evidence