Methyl 3-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate → Methyl 3-(1-aminoethyl)benzoate

HRID 1255834Notes

Reaction equation

HRID 1255834 reaction equation
C(OC([NH:8][CH:9]([C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])[CH3:10])=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH2:8][CH:9]([C:11]1[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])[CH3:10]

Participants

4

Reactant 1

HCID 68656133Methyl 3-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

Product 1

HCID 19933442Methyl 3-(1-aminoethyl)benzoateYield 100.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of methyl 3-{1-[(tert-butoxycarbonyl)amino]ethyl}benzoate (200 mg, 0.72 mmol) in 20% trifluoroacetic acid in dichloromethane (10 mL) was stirred at room temperature for 1.5 hours. After this time the mixture was concentrated under reduced pressure and the residue was dissolved in water and basified to pH 11 with aqueous ammonia. The mixture was extracted with ethyl acetate (2×15 mL) and the extracts were washed with brine (20 mL), dried (Na2SO4) and concentrated under reduced pressure to give methyl 3-(1-aminoethyl)benzoate (130 mg, 100%) as a pale yellow oil.

Workup

  1. concentrationAfter this time the mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water and basified to pH 11 with aqueous ammonia
  3. extractionThe mixture was extracted with ethyl acetate (2×15 mL)
  4. washthe extracts were washed with brine (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f999f13fc8ee473c8a84b583daf83d99
Source dataset
uspto-grants-2013_06
Patent number
US08461161B2

Reaction notes

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