反应详情

To a solution of 428 g (959 mmol) of (3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-1-((S)-1-hydroxybutan-2-yl)-3-methylpiperidin-2-one (Example 151, Step A) in dichloromethane (4.55 L) was added 25.9 mL (1.44 mol) of water. A solution of 610 g (1.44 mol) of Dess-Martin periodinane in dichloromethane (4.55 L) was added slowly over a 25 min period so as to maintain an internal reaction temperature not exceeding 25° C. The white slurry was stirred for 2.5 h and then was quenched by cautious, slow addition of saturated aqueous sodium thiosulfate (5.2 L) so as to maintain an internal reaction temperature below 30° C. Water was added and the mixture was extracted with dichloromethane (3×). The combined organic layers were washed with saturated aqueous sodium bicarbonate solution (4×) and then saturated aqueous sodium chloride (1×), dried over Na2SO4, filtered and the filtrate was concentrated to afford a yellow oily solid. A mixture of ethyl ether and DCM were added, and precipitated solids were filtered off. The precipitation/filtration process was repeated. The filtrate was concentrated to provide the title compound as a white solid. The crude product was used directly in the next step.

1. temperatureto maintain an internal reaction temperature not
2. customexceeding 25° C
3. customwas quenched by cautious,
4. additionslow addition of saturated aqueous sodium thiosulfate (5.2 L) so as
5. temperatureto maintain an internal reaction temperature below 30° C
6. additionWater was added
7. extractionthe mixture was extracted with dichloromethane (3×)
8. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution (4×)
9. dry with materialsaturated aqueous sodium chloride (1×), dried over Na2SO4
10. filtrationfiltered
11. concentrationthe filtrate was concentrated
12. customto afford a yellow oily solid
13. additionwere added
14. customprecipitated solids
15. filtrationwere filtered off
16. concentrationThe filtrate was concentrated