Methylamine → HCID 11098956, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Example 3 (2.80 g, 12.4 mmol) in ethanol (45 mL), pyrrolidine (3.3 mL, 39.5 mmol) was added. The reaction was heated to reflux for 2.5 hours then all volatiles removed in vacuo. This was then dissolved in diethyl ether (60 mL), cooled to 0° C., and flushed with argon. Triethylamine (5.5 mL, 39 mmol) was added followed by methanesulphonyl chloride (1.2 mL, 16 mmol), and the reaction was stirred for 30 minutes. More triethylamine (3.7 mL, 26 mmol) was added, the reaction was warmed to room temperature over 30 minutes, then an aqueous solution of methylamine (40% w/w) (19 mL, 220 mmol) and water (16 mL) were added. After stirring for 18.5 hours, the layers were separated, and the aqueous layer was extracted with diethyl ether (3×100 mL). The combined organics were washed with 5% sodium bicarbonate solution (60 mL), water (60 mL) and brine (60 mL), dried (MgSO4), and the solvent removed in vacuo. Purification by column chromatography (dichloromethane:methanol 9:1→dichloromethane:methanol:ammonia 40:9:1) gave the product as a yellow semi-solid, 9.0 mmol, 72%.

Provenance & Evidence