2,3-Dihydroxybutanedioic Acid → (1RS,5RS)-4-(4-chlorobenzyl)-1-methyl-6-oxa-bicyclo[3,2,0]heptane-5-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In 12 ml of toluene, 267 mg of Compound 5-1 obtained in Production Example 9 of Example 1 described above was dissolved. The solution thus obtained was then cooled to −78° C. To the solution thus cooled, 1.2 ml of hexane solution of 1.0M diisobutylaluminum hydride was added dropwise. Thereafter, the resulting mixture solution was stirred for 1 hour. After the reaction, 1 ml of methanol and 10 ml of 10% aqueous solution of tartaric acid were added to the reaction solution thus obtained. The resulting mixture solution was stirred for 0.5 hour while being allowed to reach room temperature. The reaction solution thus obtained was mixed with saturated brine, and extraction with ethyl acetate was then carried out. The organic layers thus extracted were blended with each other and then washed with saturated brine. Thereafter, the organic layers were dried over anhydrous sodium sulfate, and the solvent was distilled away under a reduced pressure. The residue was purified by silica gel column chromatography to obtain 184 mg of Compound 15-1.

Provenance & Evidence