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

Temperature

-78 °C

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.

1. dissolutionabove was dissolved
2. customThe solution thus obtained
3. temperatureTo the solution thus cooled
4. additionwere added to the reaction solution
5. customthus obtained
6. stirringThe resulting mixture solution was stirred for 0.5 hour
7. customto reach room temperature
8. customThe reaction solution thus obtained
9. extractionThe organic layers thus extracted
10. washthen washed with saturated brine
11. dry with materialThereafter, the organic layers were dried over anhydrous sodium sulfate
12. distillationthe solvent was distilled away under a reduced pressure
13. customThe residue was purified by silica gel column chromatography

ORD record

ord-2e5573810a774db4ab42351902a50c04

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09278966B2