Indole → Cinchonine

HRID 450836

Reaktionsgleichung

N1C2C(=CC=CC=2)C=C1.[CH2:10]=[CH:11][C@@H:12]1[C@@H:17]2[CH2:18][C@@H:19]([C@H:20]([OH:31])[C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=[CH:23][CH:22]=3)[N:14]([CH2:15][CH2:16]2)[CH2:13]1>>[CH2:10]=[CH:11][C@@H:12]1[C@@H:17]2[CH2:18][C@H:19]([C@@H:20]([OH:31])[C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=[CH:23][CH:22]=3)[N:14]([CH2:15][CH2:16]2)[CH2:13]1

Komponenten

Edukt 2

HCID 798Indole

HCID 101744Cinchonidine

Produkt 1

HCID 90454Cinchonine

Versuchsvorschrift

Chemical resolution of the 2-carboxyl derivative of 3-phosphoindoles of Formula I/II was performed on 280.82 g of 1 using (−)-Cinchonidine 2 (Scheme 15, to obtain the required enantiomer, first eluting isomer by chiral HPLC analysis) and (+)-Cinchonine 3 (which can be used to remove the undesired enantiomer from the filtrate, second eluting isomer by chiral HPLC analysis).

Quellen und Nachweise

ORD-Eintrag: ord-6338ba3c736f425484121c5e33583895
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08486991B2

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