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

HRID 1293168Notes

Reaction equation

HRID 1293168 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 (12.83 g, 45.9 mmol) was treated with trifluoroacetic acid (100 mL) and dichloromethane (100 mL) at room temperature for 16 h. 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 ethyl acetate to give 9.40 g (95%) of the title compounds as white solids: 1H-NMR (DMSO-d6) δ 8.67 (2H, br.s), 8.01 (2H, d, J=8.4 Hz), 7.68 (2H, d, J=8.4 Hz), 4.49 (1H, q, J=6.9 Hz), 3.87 (3H, s), 1.53 (3H, d, J=6.9 Hz).

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 ethyl acetate

Sources & evidence

ORD record
ord-9fd66a3130954625820424c14a6e127d
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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