반응 #44478

반응 방정식

O-phosphoric acid

ethyl acetate

imidazole

Tert-butyl-chloro-dimethyl-silane

Sodium borohydride

solution

1-Cycloheptyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

→

title compound

4-(tert-Butyl-dimethyl-silanyloxymethyl)-1-cycloheptyl-pyrrolidine-2-one

용매

methanol

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction was cooled to 0° C.
2. 2
   workup.STIRRINGstirred
3. 3
   여과The reaction was filtered through a pad of celite
4. 4
   세척rinsed with methanol
5. 5
   농축concentrated under vacuo
6. 6
   세척washed with water (25 mL)
7. 7
   건조The organic layer was dried with MgSO4
8. 8
   여과filtered
9. 9
   기타evaporated in vacuo
10. 10
    workup.STIRRINGstirred for three hours
11. 11
    세척washed with water (50 mL) and brine (25 mL)
12. 12
    건조The organic layer was dried with MgSO4
13. 13
    여과filtered
14. 14
    기타evaporated in vacuo
15. 15
    기타The crude product was purified by flash chromatography (hexanes:ethyl acetate 95:5 to 75:25)

실험 절차

Sodium borohydride (0.213 g, 5.77 mmoles) was added to a solution of Example 1A (0.7 g, 2.92 mmoles) in methanol (3 mL) and tetrahydrofuran (3 mL) and stirred at 60° C. for two hours. The reaction was cooled to 0° C. and O-phosphoric acid (1.6 g, 17.4 mmoles) was added and stirred. The reaction was filtered through a pad of celite, rinsed with methanol, and concentrated under vacuo. The crude oil was taken up in ethyl acetate (25 mL) and washed with water (25 mL). The organic layer was dried with MgSO4, filtered and evaporated in vacuo. The resulting oil was taken up in N,N-dimethylformamide (4 mL) and imidazole (391 g, 5.76 mmoles) and Tert-butyl-chloro-dimethyl-silane (583 g, 3.88 mmoles) were added and stirred for three hours. The reaction was diluted with ethyl acetate (40 mL) and washed with water (50 mL) and brine (25 mL). The organic layer was dried with MgSO4 filtered and evaporated in vacuo. The crude product was purified by flash chromatography (hexanes:ethyl acetate 95:5 to 75:25) to give the title compound as a colorless oil.

출처