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

HRID 1425297
Notes
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Reaction equation

HRID 1425297 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-88512e33c4374994955c8378833d9a9f
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927588B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes