N-Methylbenzamide → HCID 19029150, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-methylbenzamide (0.38 g) in 200 mL of anhydrous tetrahydrofuran was cooled to -78° C. and treated with tert-butyl lithium (30 mL, 1.7M). At the end of the addition, the reaction mixture was allowed to warm to 0° C. and stirred at this temperature for 1 hour and then cooled back to -78° C. After treatment with a solution of 1-benzyloxycarbonyl-4-piperidone (5.83 g) in 2 mL of tetrahydrofuran, the reaction mixture was stirred at -78° C. for 40 minutes and then quenched with 300 mL of saturated ammonium chloride solution. Extraction with ethyl acetate, washing the organic layer with brine, drying over magnesium sulfate and evaporation afforded the crude product. This material was partially purified by column chromatography; elution with ethyl acetate:hexane (6:4) afforded the named material (5.25 g); MS: 238 (M-99); NMR: 1.6-1.7 (m, 2), 2.0-2.1 (m, 2), 3.4 (br., 2), 4.0-4.1 (br, 2), 5.2(s, 1), 7.2-7.4 (m, 5), 7.5 (m, 1), 7.7 (m, 1), 7.9 (m, 1).

Provenance & Evidence