تفاعل #1935682

معادلة التفاعل

tert-butyl 1-oxo-2-(5-oxo-4-vinyl-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

sodium periodate

→

title compound

tert-butyl 2-(4-formyl-5-oxo-2,5-dihydrofuran-3-yl)-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

المذيبات

water

acetone

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction temperature was maintained below 40° C.
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 1 hour at room temperature
3. 3
   workup.WAITLCMS after 2 hours showed complete
4. 4
   أخرىconsumption of starting material
5. 5
   ترشيحThe suspension was filtered
6. 6
   تركيزthe filtrate was concentrated
7. 7
   أخرىto remove acetone
8. 8
   استخلاصThe aqueous layer was extracted with DCM (3×)
9. 9
   غسيلCombined organic layers were washed with 10% Na2S2O3 solution (2×)
10. 10
    تجفيفdried over anhydrous Na2SO4
11. 11
    ترشيحfiltered
12. 12
    تركيزconcentrated

الإجراء التجريبي

tert-butyl 1-oxo-2-(5-oxo-4-vinyl-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate (1.6 g, 4.4 mmol) was dissolved in acetone (36 mL) and water (36 mL), then K2OsO4.2H2O was added and the mixture was stirred for ˜5 min. Solid sodium periodate (3.77 g, 17.6 mmol) was added in 4 portions during 1 hour and the reaction temperature was maintained below 40° C. using an ice-bath. The resulting mixture was stirred for 1 hour at room temperature. LCMS after 2 hours showed complete consumption of starting material. The suspension was filtered and the filtrate was concentrated to remove acetone. The aqueous layer was extracted with DCM (3×). Combined organic layers were washed with 10% Na2S2O3 solution (2×), dried over anhydrous Na2SO4, filtered, concentrated to obtain the title compound, which was taken to the next step without further purification.

المصدر