4-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione → 10-Aminocamptothecin

HRID 2418791

Reaktionsgleichung

Reaktionsgleichung von HRID 2418791
[CH3:1][CH2:2][C:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=[CH:20]2)=[O:11]>C(O)C.O1CCOCC1.[Pt]=O>[CH3:1][CH2:2][C@@:3]1([OH:29])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:16](=[CH:17][C:4]1=2)[C:15]1[N:18]=[C:19]2[C:24](=[CH:25][C:14]=1[CH2:13]3)[CH:23]=[C:22]([NH2:26])[CH:21]=[CH:20]2)=[O:11]

Komponenten

5

Edukt 1

HCID 655674-Ethyl-4-hydroxy-9-nitro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione

Produkt 1

HCID 10498610-AminocamptothecinAusbeute 96,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 82844Platinum oxide (PtO)KatalysatorHCID 702EthanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

10-Nitrocamptothecin (108 mg, 0.275 m-mol) is dissolved in ethanol (30 ml) and dioxane (20 ml). To this solution is added platinum oxide (20 mg), and the mixture is subjected to catalytic reduction for 30 minutes at room temperature under normal pressure. The catalyst is removed by filtration and the reaction mixture is evaporated under reduced pressure until dryness whereby 96 mg (yield: 96.2%) of 10-aminocamptothecin is obtained as a yellowish brown solid.

Aufarbeitung

  1. customThe catalyst is removed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-1603585dc78d40eaa3545e33fc671fe4
Quelldatensatz
uspto-grants-1984_09
Patentnummer
US04473692

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