Methanol → 1-Benzyloxycarbonyl-3-hydroxymethyl-1,2,5,6-tetrahydropyridine
Reaktionsgleichung
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]=[C:13]([C:17](OC)=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]=[C:13]([CH2:17][OH:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of the compound of step 1 (2.0 g, 7.33 mmol) in tetrahydrofuran (30 ml) at -20° C. was added DIBAL-H. The mixture was warmed up to 0° C. and stirred at this temperature for 5 hours. Addition of methanol (5 ml) at 0° C. followed by addition of a saturated solution of Rochelle salt (10 ml) resulted in the formation of a white slurry. After stirring for an additional 2 hours, this was filtered; the filtrate was extracted with ether and the organic layer was washed with brine and dried over magnesium sulfate. Upon evaporation, the title compound was obtained as a slightly yellow oil (1.14 g, 4.6 mmol, 63% yield).
Aufarbeitung
- customresulted in the formation of a white slurry
- stirringAfter stirring for an additional 2 hours
- filtrationthis was filtered
- extractionthe filtrate was extracted with ether
- washthe organic layer was washed with brine
- dry with materialdried over magnesium sulfate
- customUpon evaporation
Quellen und Nachweise
- ORD-Eintrag
- ord-9337a555813441a3af535f55f968b96c
- Quelldatensatz
- uspto-grants-1992_11
- Patentnummer
- US05164402
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