Vincamine → (+)-Apovincaminic acid

HRID 1632287

Reaktionsgleichung

Reaktionsgleichung von HRID 1632287
[CH3:1][CH2:2][C@:3]12[CH2:19][C@:18](O)([C:20]([O:22]C)=[O:21])[N:17]3[C:9]4=[C:10]([CH2:25][CH2:26][N:7]([C@@H:8]14)[CH2:6][CH2:5][CH2:4]2)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=13.CC[C@]12C=C(C(OC)=O)N3C4=C(CCN([C@@H]14)CCC2)C1C=CC=CC=13>O>[CH3:1][CH2:2][C@:3]12[CH:19]=[C:18]([C:20]([OH:22])=[O:21])[N:17]3[C:9]4=[C:10]([C:11]5[C:16]3=[CH:15][CH:14]=[CH:13][CH:12]=5)[CH2:25][CH2:26][N:7]([C@@H:8]14)[CH2:6][CH2:5][CH2:4]2

Komponenten

4

Edukt 2

HCID 15376VincamineHCID 71204Apovincamine

Produkt 1

HCID 160154(+)-Apovincaminic acidAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

According to the Hungarian Patent Specification No. 163,143 racemic, cis compounds of the formula (I) and optically active, cis compound of the formula (Ic) were prepared by hydrolyzing the pharmaceutically active vincamine and converting the vincaminic acid obtained into a desired ester from which the corresponding apovincaminic acid ester was obtained by splitting off water; or alternatively, vincamine was first converted into apovincamine by splitting off water which was then subjected to hydrolysis and the apovincaminic acid obtained was converted into a desired ester. This process is disadvantageous in that at first vincamine should be prepared by a multi-step synthesis from which the corresponding apovincaminic acid esters can be prepared with a yield of at most 60% only.

Aufarbeitung

  1. customwas then subjected to hydrolysis

Quellen und Nachweise

ORD-Eintrag
ord-44d6c4a287d4486689885cbf94ee5dfd
Quelldatensatz
uspto-grants-1984_10
Patentnummer
US04474960

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