Reaktion #8861

Reaktionsgleichung

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

Ausbeute 66.7%

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

Ausbeute 66.7%

Lösungsmittel

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas then quenched with isopropanol
2. 2
   workup.ADDITIONThe mixture was diluted with water
3. 3
   Extraktionextracted three times with methylene chloride
4. 4
   WaschenThe combined organic layers were washed with brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified by flash chromatography
9. 9
   Wascheneluting with 20% ethyl acetate in hexanes

Vorschrift

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).

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