Réaction #70816

Équation de réaction

(7S,8R)-8-Benzamido-1,4-dioxaspiro[4.5]decane-7-carboxylic acid

HCl

→

(1S,2R)-2-benzamido-5-oxocyclohexanecarboxylic acid

Rendement 67.0%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe reaction stirred at 25° C. for about 16 hours
2. 2
   ConcentrationThe reaction was concentrated
3. 3
   Autreto remove the acetonitrile
4. 4
   AutreWhite solids precipitated
5. 5
   workup.ADDITIONethyl acetate and THF were added
6. 6
   workup.DISSOLUTIONto dissolve the solids
7. 7
   LavageThe resulting mixture was rinsed (3×) with water
8. 8
   SéchageThe organic layer was dried over sodium sulfate
9. 9
   Concentrationconcentrated

Mode opératoire

(7S,8R)-8-Benzamido-1,4-dioxaspiro[4.5]decane-7-carboxylic acid (750 mg, 2.456 mmol) was dissolved in acetonitrile (10 mL) at 25° C. with stirring. 1N HCl (12.28 mL, 12.28 mmol) was then added thereto and the reaction stirred at 25° C. for about 16 hours. The reaction was concentrated to remove the acetonitrile. White solids precipitated and ethyl acetate and THF were added to dissolve the solids. The resulting mixture was rinsed (3×) with water. The organic layer was dried over sodium sulfate and concentrated to give (1S,2R)-2-benzamido-5-oxocyclohexanecarboxylic acid (430 mg, 1.646 mmol, 67.0% yield) as a white solid. MS (ESI+)=262.11 (M+H)+.

Source