Dichloromethane → 4-Amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochloride

HRID 433288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 433288
C(OC([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH3:24])[CH:15]=1)[CH2:10][CH:11]([OH:13])[CH3:12])=O)(C)(C)C.O1CCOCC1.C(Cl)[Cl:32]>>[ClH:32].[NH2:8][CH:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:23][CH3:24])[CH:15]=1)[CH2:10][CH:11]([OH:13])[CH3:12]

Komponenten

4

Edukt 3

HCID 6344DichloromethaneHCID 312751,4-DioxaneHCID 131724264Tert-butyl (1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl)carbamate

Produkt 1

HCID 187583154-Amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochlorideAusbeute 85 %

Versuchsvorschrift

A mixture of (tert-butoxy)-N-[1-(3-ethoxy-4-methoxyphenyl)-3-hydroxybutyl]carboxamide (0.98 g, 2.89 mmol) and 4Nhydrochloric acid/dioxane (3 mL) in methylene chloride (10 mL) was stirred at room temperature for 16 hours. The resulting slurry was filtered and washed with ethyl acetate to give 4-amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochloride as a white solid (0.68 g, 85%); 1H NMR (D2O) δ7.12 (m, 3H), 4.47 (t, J=7.0 Hz, 1H), 4.20 (q, J=7.4 Hz, 2H), 3.90 (s, 3H), 3.83-3.76 (m, 1H), 2.21-2.15 (m, 2H), 1.43 (t, J=6.9 Hz, 3H), 1.24 (d, J=6.1 Hz, 3H); 13C NMR (D2O) δ151.75, 150.48, 131.92, 123.09, 115.05, 114.54, 67.86, 66.98, 58.53, 55.35, 44.41, 24.49, 16.68.

Aufarbeitung

  1. filtrationThe resulting slurry was filtered
  2. washwashed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b283f32193fb41d7abc60ed61d523cc3
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667316B1

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