反応 #44478

反応方程式

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

溶媒

methanol

tetrahydrofuran

反応条件

後処理

1. 1
   温度The reaction was cooled to 0° C.
2. 2
   workup.STIRRINGstirred
3. 3
   ろ過The reaction was filtered through a pad of celite
4. 4
   洗浄rinsed with methanol
5. 5
   濃縮concentrated under vacuo
6. 6
   洗浄washed with water (25 mL)
7. 7
   乾燥The organic layer was dried with MgSO4
8. 8
   ろ過filtered
9. 9
   その他evaporated in vacuo
10. 10
    workup.STIRRINGstirred for three hours
11. 11
    洗浄washed with water (50 mL) and brine (25 mL)
12. 12
    乾燥The organic layer was dried with MgSO4
13. 13
    ろ過filtered
14. 14
    その他evaporated in vacuo
15. 15
    その他The crude product was purified by flash chromatography (hexanes:ethyl acetate 95:5 to 75:25)

実験手順

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.

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