Potassium bisulfate → HCID 57771527, compound

Participants

Reaction Steps

To a solution of the crude product (5.23 g) containing 3-oxo-spiro[4.4]nonane-2-carboxylic acid benzyl ester obtained in Step 3 in methanol (100 mL) was added sodium borohydride (254 mg) under ice-cooling, followed by stirring under ice-cooling for 30 minutes. Then, after addition of 10% aqueous potassium hydrogen sulfate solution (10 mL) to the reaction mixture, methanol was evaporated off in vacuo, followed by extraction with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate (volume ratio)=10:1 to 3:1) to give 3-hydroxy-spiro[4.4]nonane-2-carboxylic acid benzyl ester (less-polar isomer; 1.29 g, more-polar isomer; 2.23 g).

Provenance & Evidence