Methyl iodide → HCID 15096756, compound

Participants

Reaction Conditions

Reaction Steps

1-Phenylmethyl-3-hydroxy-4,4-dimethoxypiperidine (3b, 5.5 g, 22 mmol) from Example 1 in 30 ml of dimethylformamide was added slowly to a stirred suspension of sodium hydride (0.81 g, 27 mmol, 80% oil suspension) in 100 ml of dimethylformamide. The reaction mixture was warmed to 60° C. for 2 hours, then cooled to 0° C. whereupon methyl iodide (3.8 g, 27 mmol) was slowly added to the mixture. The reaction mixture was stirred overnight at room temperature then quenched with 10 ml of 10% sodium hydroxide solution. The reaction mixture was concentrated under vacuum, the residue slurried in 300 ml of water and the aqueous mixture extracted with 3×100 ml of ether. The combined organic layers were dried over magnesium sulfate, concentrated under vacuum, then purified by column chromatography (alumina; ethyl acetate/hexane; 2.5:1) to yield the intermediate 1-phenylmethyl-3-methoxy-4,4-dimethoxypiperidine (4b, 3.77 g, 64.6%, Rf 0.63).

Provenance & Evidence