1,4-Dioxane → 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid

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Reaktionsgleichung

C(N(CC)[C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH2:15][C@H:16]([NH:18][CH2:19][C@@H:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[OH:21])[CH3:17])=[O:5])C.[O:31]1CCOCC1>Cl>[Cl:28][C:24]1[CH:23]=[C:22]([C@@H:20]([OH:21])[CH2:19][NH:18][C@H:16]([CH3:17])[CH2:15][C:11]2[C:10]3[C:14](=[C:6]([C:4]([OH:31])=[O:5])[CH:7]=[CH:8][CH:9]=3)[NH:13][CH:12]=2)[CH:27]=[CH:26][CH:25]=1

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

A solution of 3-{(2 R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethyl-amino]propyl}-1H-indole-7-carboxylic acid diethylamide (175 mg, 0.41 mmol) in 1,4-dioxane (7 mL) and 6N hydrochloric acid (7 mL) is stirred with heating at 150° C. for 7 hours in a closed system. After cooling, the mixture is evaporated under reduced pressure to remove dioxane, and the resultant is neutralized with an aqueous Na2CO3 solution. The precipitates are filtered, and purified by reversed phase column (octa-decylsilyl, methanol/water=1/1→3/1) to give the desired 3-{(2R)-2-[2-(3-chlorophenyl)-(2R)-2-hydroxyethylamino]propyl}-1H-indole-7-carboxylic acid (45 mg, yield: 30%).

Aufarbeitung

temperatureAfter cooling
customthe mixture is evaporated under reduced pressure
customto remove dioxane
filtrationThe precipitates are filtered
custompurified by reversed phase column (octa-decylsilyl, methanol/water=1/1→3/1)

Quellen und Nachweise

ORD-Eintrag: ord-46ccc422023c4242b73ea0d0a0dbc462
Quelldatensatz: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07217724B2

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