Dichloromethane → (S)-Methyl 4-(1-aminoethyl)benzoate hydrochloride

HRID 493521Notes

Reaction equation

HRID 493521 reaction equation
C(OC([NH:8][C@H:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.FC(F)(F)C(O)=O.[Cl:28]CCl>>[ClH:28].[NH2:8][C@H:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)[CH3:10]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 57432297(S)-Methyl 4-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

Product 1

HCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochlorideYield 95%

Procedure

Methyl 4-{(1S)-1-[(tert-butoxycarbonyl)amino]ethyl}benzoate (step 4, 12.83 g, 45.9 mmol) was treated with trifluoroacetic acid (100 mL) and dichloromethane (100 mL) at room temperature for 16 hours. After removal of the solvent, the residue was diluted with 10% hydrogen chloride solution in methanol (100 mL). The mixture was concentrated under reduced pressure and the residue was washed with ethylacetate to give 9.40 g (95%) of the title compound as white solids:

Workup

  1. customAfter removal of the solvent
  2. additionthe residue was diluted with 10% hydrogen chloride solution in methanol (100 mL)
  3. concentrationThe mixture was concentrated under reduced pressure
  4. washthe residue was washed with ethylacetate

Sources & evidence

ORD record
ord-4517a9053b24492694c1fbbd7e73cbfd
Source dataset
uspto-grants-2009_05
Patent number
US07534914B2

Reaction notes

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