Hydrochloric Acid → (S)-Methyl 4-(1-aminoethyl)benzoate hydrochloride

HRID 1476738Notes

Reaction equation

HRID 1476738 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.[ClH:21]>>[ClH:21].[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

3

Reactant 2

HCID 313Hydrochloric AcidHCID 57432297(S)-Methyl 4-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

Product 1

HCID 57462942(S)-Methyl 4-(1-aminoethyl)benzoate hydrochlorideYield 97.1%

Procedure

To methyl (S)-4-(1-tert-butoxycarbonylaminoethyl)benzoate (1.00 g, 3.58 mmol), add hydrogen chloride (4 M in dioxane, 5 mL, 20 mmol) and stir the resulting mixture at room temperature for one hour. Concentrate the mixture under reduced pressure to furnish the title compound as a white solid (750 mg, 97% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.57 (br s, 3H), 7.99 (d, J=8.4 Hz, 2H), 7.65 (d, J=8.4 Hz, 2H), 4.47 (q, J=6.7 Hz, 1H), 3.84 (s, 3H), 1.50 (d, J=6.8 Hz, 3H).

Workup

  1. concentrationConcentrate the mixture under reduced pressure

Sources & evidence

ORD record
ord-3c375dfaeeed458da4c91bd4104820c2
Source dataset
uspto-grants-2016_08
Patent number
US09402838B2

Reaction notes

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