تفاعل #8861

معادلة التفاعل

tert-butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

tert-Butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate

Jones reagent

→

title compound

المردود 66.7%

tert-Butyl 1-(1-oxoprop-1-yl)-2-oxo-8-azaspiro[4.5]decane-8-carboxylate

المردود 66.7%

المذيبات

acetone

ظروف التفاعل

المعالجة

1. 1
   أخرىwas then quenched with isopropanol
2. 2
   workup.ADDITIONThe mixture was diluted with water
3. 3
   استخلاصextracted three times with methylene chloride
4. 4
   غسيلThe combined organic layers were washed with brine
5. 5
   تجفيفdried over sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was purified by flash chromatography
9. 9
   غسيلeluting with 20% ethyl acetate in hexanes

الإجراء التجريبي

To a solution of tert-butyl 1-(1-hydroxyprop-1-yl)-2-hydroxy-8-azaspiro[4.5]decane-8-carboxylate (0.050 g, 0.16 mmol) from Step E in acetone (2 mL) at 0° C. was added 2.6M Jones reagent (0.122 mL, 0.32 mmol). The reaction was stirred at room temperature for 10 min and was then quenched with isopropanol. The mixture was diluted with water and extracted three times with methylene chloride. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography eluting with 20% ethyl acetate in hexanes to afford the title compound (0.033 g).

المصدر