Reaction #8861

Reaction equation

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

Yield 66.7%

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

Yield 66.7%

Solvents

acetone

Conditions

Workup

1. 1
   Otherwas then quenched with isopropanol
2. 2
   workup.ADDITIONThe mixture was diluted with water
3. 3
   Extractionextracted three times with methylene chloride
4. 4
   WashThe combined organic layers were washed with brine
5. 5
   Dryingdried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   OtherThe residue was purified by flash chromatography
9. 9
   Washeluting with 20% ethyl acetate in hexanes

Procedure

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).

Source