反应详情

温度

0 °C

2.4 ml (1.26 mmol) of 20% suspension Nysted reagent and 6.4 ml of tetrahydrofuran were added dropwise to a reactor successively and cooled to 0° C. 0.14 ml (1.26 mmol) of TiCl4 was added thereto dropwise, and the resulting mixture was stirred. The reaction mixture was cooled to −40° C., and a solution which had been prepared by dissolving 0.527 g (0.842 mmol) of 3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-2-trityloxymethyl-cyclopentanone (a compound of formula (2)) obtained in Example 2 in 2.4 ml of tetrahydrofuran was added thereto. The reaction mixture was stirred at room temperature for 3.5 hrs. After completion of the reaction, the reaction mixture was cooled to −20° C., quenched by adding 25 ml of 1N hydrochloric acid, and extracted with 25 ml of dichloromethane to separate an organic layer. The organic layer was washed with 20 ml of 4% sodium bicarbonate solution and 20 ml of brine successively, dried over anhydrous sodium sulfate, filtered, and condensed. The residue thus obtained was isolated by HPLC to obtain 0.184 g of the title compound (yield: 50%).

1. temperatureThe reaction mixture was cooled to −40° C.
2. customa solution which had been prepared
3. additionwas added
4. stirringThe reaction mixture was stirred at room temperature for 3.5 hrs
5. customAfter completion of the reaction
6. temperaturethe reaction mixture was cooled to −20° C.
7. customquenched
8. additionby adding 25 ml of 1N hydrochloric acid
9. extractionextracted with 25 ml of dichloromethane
10. customto separate an organic layer
11. washThe organic layer was washed with 20 ml of 4% sodium bicarbonate solution and 20 ml of brine successively
12. dry with materialdried over anhydrous sodium sulfate
13. filtrationfiltered
14. customcondensed
15. customThe residue thus obtained
16. customwas isolated by HPLC