反应详情

A solution of (cis)-3-azido-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-oxoazetidine (6 g, 18.75 mmole) in 1:1 ethanol-dichloromethane (180 ml) was cooled to -78° C. and ozonized until the mixture retained a purple hue. The reaction was purged with nitrogen, and sodium borohydride (2.835 g, 75 mmole) was added as a solid followed by 85 ml of ethanol. The mixture is allowed to stand at -78° C. for five minutes and then stirred at ice-bath temperature for one hour. The reaction was acidified to pH 4 with 3N hydrochloric acid, and the solvents were removed in vacuo. The residue was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate and the organic extracts were washed with saturated potassium bicarbonate, brine, dried (sodium sulfate), filtered, and concentrated to a solid which was treated with ether. After standing under ether for three hours at 5° C., the white solid was filtered, washed with fresh ether, hexane, and dried under high vacuum. The yield of the title compound was 3.333 g.

1. additionwas added as a solid
2. customthe solvents were removed in vacuo
3. customThe residue was partitioned between water and ethyl acetate
4. extractionThe aqueous layer was extracted with additional ethyl acetate
5. washthe organic extracts were washed with saturated potassium bicarbonate, brine
6. dry with materialdried (sodium sulfate)
7. filtrationfiltered
8. concentrationconcentrated to a solid which
9. additionwas treated with ether
10. waitAfter standing under ether for three hours at 5° C.
11. filtrationthe white solid was filtered
12. washwashed with fresh ether, hexane
13. customdried under high vacuum