3,3-Dimethylbutanoyl chloride → HCID 11639474, compound

Participants

Reaction Steps

To a solution of 4-(ethylsulfonyl)-N′-(tetrahydro-2H-pyran-4-ylmethyl)benzene-1,2-diamine (Step B) in ethyl acetate (16 mL) was added tert-butylacetyl chloride (0.1 mL, 0.8 mmol) at room temperature. After stirring for 2 h, the mixture was quenched with water and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The residue was dissolved in ethanol and 2N sodium hydroxide solution. The mixture was microwaved for 30 min at 130° C. The reaction mixture was quenched with water and extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure. The residue was purified by amine coated silica gel column chromatography (hexane:ethyl acetate=2:1 as eluent) to afford the title compound (103 mg, 34%) as a white solid.

Provenance & Evidence