Reacción #8861

Ecuación de reacción

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

Rendimiento 66.7%

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

Rendimiento 66.7%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowas then quenched with isopropanol
2. 2
   workup.ADDITIONThe mixture was diluted with water
3. 3
   Extracciónextracted three times with methylene chloride
4. 4
   LavadoThe combined organic layers were washed with brine
5. 5
   Secadodried over sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was purified by flash chromatography
9. 9
   Lavadoeluting with 20% ethyl acetate in hexanes

Procedimiento

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).

Fuente