Ethyl 3-(4-tert-butoxycarbonylaminocyclohex-1-enyl)benzoate → Ethyl 3-(4-aminocyclohex-1-enyl)benzoate

HRID 43832Notes

Reaction equation

HRID 43832 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH2:10]1)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:11][CH2:10]1

Participants

3

Reactant 1

HCID 67548489Ethyl 3-(4-tert-butoxycarbonylaminocyclohex-1-enyl)benzoate

Product 1

HCID 67549303Ethyl 3-(4-aminocyclohex-1-enyl)benzoateYield 57.8%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

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.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in methanol
  3. additionAmberlite IRA-400(Cl) ion exchange resin (20 g) was added
  4. stirringthe mixture was stirred at room temperature for one hour
  5. filtrationAmberlite was filtered off
  6. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bf23ea28f6034bdda8416854eaad78ca
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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