Reaktion #70816

Reaktionsgleichung

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

HCl

→

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

Ausbeute 67.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

(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)+.

Quelle