Methyl 7-(2,2-dimethylpropionylamino)-3-hydroxychroman-8-carboxylate → Methyl 7-(2,2-dimethylpropionylamino)-3-oxochroman-8-carboxylate

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Reaction Steps

1,1,1-Tris-(acetoxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess Martin periodinane, 5.65 g) was added to a stirred solution of methyl 7-(2,2-dimethylpropionylamino)-3-hydroxychroman-8-carboxylate (Intermediate 11, 3.41 g) in DCM (50 mL) and the resultant mixture was stirred at room temperature for 5 hours. The resulting solution was washed with a 10% solution of sodium thiosulphate in saturated sodium bicarbonate solution, dried (Na2SO4) and filtered. The filtrate was evaporated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-30% to give methyl 7-(2,2-dimethylpropionylamino)-3-oxochroman-8-carboxylate (2.26 g) as an off-white solid.

Provenance & Evidence