2-Methyl-2-butene → HCID 89650335, compound

Participants

Reaction Steps

A solution of sodium chlorite (219 mg; 2.42 mmol; 5 eq.) and sodium dihydrogenphosphate (233 mg; 1.94 mmol; 4 eq.) in water (1 mL) was added dropwise to a mixture of 2-methyl-2-butene (1 mL) and 4-(2-formyl-phenoxy)-3-trifluoromethyl-piperidine-1-carboxylic acid tert-butyl ester (181 mg; 0.48 mmol; 1 eq.) in 1,4-dioxane (4 mL). The reaction mixture was stirred at room temperature for 1 hour and the 1,4-dioxane concentrated in vacuo. The aqueous solution was diluted with water and the pH made acidic with 0.1M HCl. The mixture was extracted with DCM (2×) and the combined organic phase was dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (86 mg, 46%) as a white solid. HPLC (max plot) 97.3%, Rt 4.39 min. UPLC/MS: (MS−) 388.3 ([M−H]−).

Provenance & Evidence