Methanol → HCID 86635315, Verbindung

HRID 656907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656907
[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH:14]=O)[C:10](=[O:16])[CH:9]=[CH:8]2)[CH3:2].[NH:18]1[CH2:23][CH2:22][CH:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:20][CH2:19]1.CO.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[C:4]([F:17])=[CH:5][N:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH2:14][N:18]1[CH2:19][CH2:20][CH:21]([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:29])([CH3:28])[CH3:30])[CH2:22][CH2:23]1)[C:10](=[O:16])[CH:9]=[CH:8]2)[CH3:2]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86635314(8-Ethyl-7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde

Produkt 1

HCID 86635315HCID 86635315, VerbindungAusbeute 77,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

(8-Ethyl-7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde (0.168 g, 0.718 mmol) and 1,1-dimethylethyl 4-piperidinylcarbamate (0.172 g, 0.860 mmol) was dissolved in CHCl3 (6 ml) and MeOH (0.6 ml) at rt under argon, whereupon NaBH(OAc)3 (0.497 g, 2.34 mmol) was added, after which it was stirred for 3 h. The reaction was then purified by chromatography on silica gel using a 0-20% MeOH in EtOAc gradient to give the title compound as a yellow oil (0.234 g, 72%).

Aufarbeitung

  1. customThe reaction was then purified by chromatography on silica gel using a 0-20% MeOH in EtOAc gradient

Quellen und Nachweise

ORD-Eintrag
ord-eee53b1a30c64937b84460dfa5c32574
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071592B2

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