Hydrochloric Acid → HCID 57771629, compound

Participants

Reaction Steps

To a solution of 9,9-dimethyl-6-oxo-spiro[4.5]decane-7-carboxylic acid methyl ester (450 mg) obtained in Step 1 in methanol (4.5 mL) was added calcium chloride dihydrate (417 mg), followed by stirring under ice-cooling for 15 minutes. Then, to the reaction mixture was added sodium borohydride (90 mg) in three portions, followed by stirring the reaction mixture under ice-cooling for 1.5 hours. To the reaction mixture were added successively 2N aqueous hydrochloric acid solution, toluene and saturated brine, and the mixture was stirred for 5 minutes, followed by separation of the aqueous layer. The organic layer was washed successively with water and saturated brine, dried and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:19 to 1:6) to give 6-hydroxy-9,9-dimethyl-spiro[4.5]decane-7-carboxylic acid methyl ester (341 mg).

Provenance & Evidence