Hydrochloric Acid → (R)-4-(1-aminoethyl)-2-methoxyphenol hydrochloride

HRID 1693056Notes

Reaction equation

HRID 1693056 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][S@@](C(C)(C)C)=O)[CH3:9])=[CH:4][C:3]=1[O:17][CH3:18].[ClH:19]>CO>[ClH:19].[NH2:10][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[C:3]([O:17][CH3:18])[CH:4]=1)[CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67278686(R)-N-((R)-1-(4-hydroxy-3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide

Product 1

HCID 67279379(R)-4-(1-aminoethyl)-2-methoxyphenol hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To (R)—N—((R)-1-(4-hydroxy-3-methoxyphenyl)ethyl)-2-methylpropane-2-sulfinamide (4.10 g, 15.1 mmol) was added 10% hydrogen chloride in methanol (40 ml), and the resulting mixture was stirred at room temperature for 3 h. The reaction mixture was evapolated and dried in vacuo to give the title compound (crude 6.75 g) as a white solid. This crude amine was used for the next step without further purification. 1H NMR (270 MHz, DMSO-d6) δ ppm 1.48 (3H, d, J=6.6 Hz), 3.79 (3H, s), 4.27 (1H, m), 6.79 (1H, d, J=8.5 Hz), 6.88 (1H, d, J=8.0 Hz), 7.17 (1H, s), 8.35 (3H, br. s), 9.18 (1H, br. s). MS (ESI) m/z 151 (M+H—NH2)+.

Workup

  1. customdried in vacuo

Sources & evidence

ORD record
ord-f477c8d4d1c043d7a767b717919e03ff
Source dataset
uspto-grants-2012_04
Patent number
US08158650B2

Reaction notes

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