تفاعل #44478

معادلة التفاعل

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

المذيبات

methanol

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was cooled to 0° C.
2. 2
   workup.STIRRINGstirred
3. 3
   ترشيحThe reaction was filtered through a pad of celite
4. 4
   غسيلrinsed with methanol
5. 5
   تركيزconcentrated under vacuo
6. 6
   غسيلwashed with water (25 mL)
7. 7
   تجفيفThe organic layer was dried with MgSO4
8. 8
   ترشيحfiltered
9. 9
   أخرىevaporated in vacuo
10. 10
    workup.STIRRINGstirred for three hours
11. 11
    غسيلwashed with water (50 mL) and brine (25 mL)
12. 12
    تجفيفThe organic layer was dried with MgSO4
13. 13
    ترشيحfiltered
14. 14
    أخرىevaporated in vacuo
15. 15
    أخرىThe crude product was purified by flash chromatography (hexanes:ethyl acetate 95:5 to 75:25)

الإجراء التجريبي

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.

المصدر