Sodium Sulfite → HCID 57771526, compound

Participants

Reaction Steps

To a solution of (3S)-3-[4-((2R,5R)-2-hydroxy-spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (195 mg) obtained in Step 9 of Example 104 in chloroform (2 mL) was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane; 259 mg) under ice-cooling, followed by stirring the mixture under ice-cooling for 3 hours and then at room temperature for 1 hour. To the reaction mixture was added aqueous sodium sulfite solution, followed by extraction with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:6 to 1:4) to give (3S)-3-[4-((5R)-2-oxo-spiro[4.5]dec-6-en-7-ylmethoxy)-phenyl]-hex-4-ynoic acid methyl ester (190 mg).

Provenance & Evidence