Sodium borohydride → N-(2-(6-(Cyclopropylmethoxy)-3-(hydroxymethyl)quinolin-2-ylamino)ethyl)acetamide
Reaktionsgleichung
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[C:10]([CH:23]=[O:24])=[CH:9]3)[CH2:3][CH2:2]1.[BH4-].[Na+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[N:12]=[C:11]([NH:16][CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[C:10]([CH2:23][OH:24])=[CH:9]3)[CH2:2][CH2:3]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a stirred solution of N-(2-(6-(cyclopropylmethoxy)-3-formylquinolin-2-ylamino)ethyl)acetamide SLA 47092 (0.35 g, 1.1 mmol) in THF (10 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.04 g, 1.1 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution. After stirring for 15 min at RT, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was removed at 40° C. under vacuum and the residue was extracted with CH2Cl2 (200 mL), washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum, to give N-(2-(6-(cyclopropylmethoxy)-3-(hydroxymethyl)quinolin-2-ylamino)ethyl)acetamide SLA 47096A as a yellow oil (0.39 g, quant. yield).
Aufarbeitung
- temperaturethen cooled in an ice bath
- custombefore quenching by addition of a 1 N aq. HCl solution
- stirringAfter stirring for 15 min at RT
- customTHF was removed at 40° C. under vacuum
- extractionthe residue was extracted with CH2Cl2 (200 mL)
- washwashed with brine (20 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-9ac091dd99ee496793f29fee6de946c3
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08772316B2
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