Methanol → (2s)-(-)-1-(4-Indolyloxy)-3-(7,8-dimethoxy-2,3,4,5-tetrahydro-1h-3-benzazepin-3-yl)-2-propanol ethanedioate

HRID 481612

Reaktionsgleichung

Reaktionsgleichung von HRID 481612
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[CH3:15][O:16][C:17]1[C:27]([O:28][CH3:29])=[CH:26][C:20]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:19]=2[CH:18]=1.[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].CO>C(OCC)(=O)C>[C:30]([OH:35])(=[O:34])[C:31]([OH:33])=[O:32].[NH:10]1[C:11]2[C:7](=[C:6]([O:5][CH2:4][C@@H:2]([OH:1])[CH2:3][N:23]3[CH2:24][CH2:25][C:19]4[CH:18]=[C:17]([O:16][CH3:15])[C:27]([O:28][CH3:29])=[CH:26][C:20]=4[CH2:21][CH2:22]3)[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9]1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 971Oxalic AcidHCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 129234297,8-Dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Produkt 1

HCID 131719697(2s)-(-)-1-(4-Indolyloxy)-3-(7,8-dimethoxy-2,3,4,5-tetrahydro-1h-3-benzazepin-3-yl)-2-propanol ethanedioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

The title compound was prepared in similar fashion from (S)-(+)-4-(oxiranylmethoxy)-1H-indole and 7,8-dimethoxy-2,3,4,5-tetrahydro-1H-3-benzazepine. The resulting free base was dissolved in ethyl acetate, and precipitated with one equivalent of oxalic acid in ethyl acetate in 48% overall yield. FDMS m/e=396 (M+ of free base). α[D]589 =-9.34 (c=0.47, methanol).

Quellen und Nachweise

ORD-Eintrag
ord-37be7e5868e54c96a21f1290090195a6
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789402

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