Reaction #72110

Reaction equation

ethyl 3-(4-tert-butoxycarbonylaminocyclohex-1-enyl)benzoate

→

title compound

Yield 57.8%

Ethyl 3-(4-aminocyclohex-1-enyl)benzoate

Yield 57.8%

Solvents

hydrochloric acid 1,4-dioxane

Conditions

Workup

1. 1
   Otherthe solvent was evaporated under reduced pressure
2. 2
   workup.DISSOLUTIONThe resulting residue was dissolved in methanol
3. 3
   workup.ADDITIONAmberlite IRA-400(Cl) ion exchange resin (20 g) was added
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature for one hour
5. 5
   FiltrationAmberlite was filtered off
6. 6
   Concentrationthe solution was concentrated under reduced pressure

Procedure

A 4 N hydrochloric acid/1,4-dioxane solution (20 mL) was added to ethyl 3-(4-tert-butoxycarbonylaminocyclohex-1-enyl)benzoate obtained in Example (195b) (510 mg, 1.48 mmol). The mixture was stirred at room temperature for one hour, and the solvent was evaporated under reduced pressure. The resulting residue was dissolved in methanol. Amberlite IRA-400(Cl) ion exchange resin (20 g) was added, and the mixture was stirred at room temperature for one hour. Amberlite was filtered off, and then the solution was concentrated under reduced pressure to obtain 210 mg of the title compound as a colorless oily substance.

Source