Dimethylformamide → 4-Amino-2-[1-(ethoxy-4-methoxyphenyl)-3-hydroxybutyl]isoindoline-1,3-dione

HRID 2244522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244522
Cl.[NH2:2][CH:3]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10](OCC)[CH:9]=1)[CH2:4][CH:5]([OH:7])[CH3:6].[NH2:19][C:20]1[CH:35]=[CH:34][CH:33]=[C:22]2[C:23](N(C(OCC)=O)[C:26](=[O:27])[C:21]=12)=[O:24].C(N([CH2:41][CH3:42])CC)C.CN(C)C=[O:46]>>[NH2:19][C:20]1[CH:35]=[CH:34][CH:33]=[C:22]2[C:21]=1[C:26](=[O:27])[N:2]([CH:3]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][C:13]=1[O:46][CH2:41][CH3:42])[CH2:4][CH:5]([OH:7])[CH3:6])[C:23]2=[O:24]

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 187583154-Amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochlorideHCID 187583363-amino-N-ethoxycarbonylphthalimide

Produkt 1

HCID 187583214-Amino-2-[1-(ethoxy-4-methoxyphenyl)-3-hydroxybutyl]isoindoline-1,3-dioneAusbeute 52 %

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 4-amino-4-(3-ethoxy-4-methoxyphenyl)butan-2-ol hydrochloride (1.0 g, 3.63 mmol), 3-amino-N-ethoxycarbonylphthalimide (0.85 g, 3.63 mmol) and triethylamine (2.37 g, 3.63 mmol) in dimethylformamide (15 mL) was heated at 80-90° C. for 16 hours. The mixture was concentrated in vacuo and the residue was stirred with methylene chloride (10 mL). The mixture was filtered and the filtrate was concentrated and purified by chromatography (silica gel, methylene chloride:ethyl acetate 8:2) to give 4-amino-2-[1-(ethoxy-4-methoxyphenyl)-3-hydroxybutyl]isoindoline-1,3-dione as a white solid (0.72 g, 52%); 1H NMR (CDCl3) δ 7.41-7.35 (m, 1H), 7.11-7.05 (m, 3H), 6.83-6.80 (m, 2H), 5.54-5.48 (dd, J=4.1 and 11.8 Hz, 1H), 5.22 (s, 2H), 4.10 (q, 2H), 3.85 (s, 3H), 3.77 (m, 1H), 2.88-2.77 (m, 1H), 2.07-1.00 (m, 1H), 1.67 (s, 1H), 1.45 (t, 3H), 1.27 (d, 3H).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. custompurified by chromatography (silica gel, methylene chloride:ethyl acetate 8:2)

Quellen und Nachweise

ORD-Eintrag
ord-230cbe6d596b48c39c9d174e0c900f75
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678825B2

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