Trifluoroacetic acid → Ethyl 2-[4-(aminomethyl)phenyl]propanoate

HRID 1428797Notes

Reaction equation

HRID 1428797 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=1)=O)(C)(C)C>ClCCl>[NH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86680232Ethyl 2-(4-((tert-butoxycarbonylamino)methyl)phenyl)propanoate

Product 1

HCID 71019413Ethyl 2-[4-(aminomethyl)phenyl]propanoateYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (6 mL) was added to a solution of ethyl 2-(4-((tert-butoxycarbonylamino)methyl)phenyl)propanoate (6.0 g, 19.54 mmol) in dichloromethane (30 mL) at 0° C. and stirred for 4 h at room temperature. The volatiles were evaporated under reduced pressure, basified with saturated NaHCO3 and extracted with ethyl acetate (3×50 mL). Combined organic layers washed with water (100 mL), brine solution (50 mL), dried over sodium sulfate and concentrated to give ethyl 2-(4-(aminomethyl)phenyl)propanoate (3.5 g, 86%) as colorless liquid.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. washCombined organic layers washed with water (100 mL), brine solution (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-089cc8461e8445f6afd961f5bb4638f2
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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