Water → rac-4-(Benzyloxy)-2-methylbutane-1,2-diamine
Reaktionsgleichung
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]([CH3:21])([CH2:11][CH2:12][O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]#[N:10].O.[OH-].[Na+]>C1COCC1>[CH2:14]([O:13][CH2:12][CH2:11][C:8]([CH3:21])([NH2:7])[CH2:9][NH2:10])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Under argon and at 0° C., 1.59 ml (1.59 mmol) of lithium aluminium hydride (1 N solution in diethyl ether) were added to 0.5 g (2.45 mmol) of 2-amino-4-(benzyloxy)-2-methylbutanonitrile Example 260A in 25 ml of dry THF. The reaction solution was stirred first at 0° C. for 30 min and then for another 1 h whilst slowly warming to room temperature. 245 μl of water, 245 μl of 2 N aqueous sodium hydroxide solution and 490 μl of water were then added carefully. The precipitate was filtered off and washed with THF and methanol, the filtrate was concentrated and the residue was purified by silica gel chromatography (mobile phase: dichloromethane/2 N ammonia in methanol=20/1, isocratic). This gave 0.30 g of the target compound (96% pure, 57% of theory).
Aufarbeitung
- temperaturefor another 1 h whilst slowly warming to room temperature
- filtrationThe precipitate was filtered off
- washwashed with THF and methanol
- concentrationthe filtrate was concentrated
- customthe residue was purified by silica gel chromatography (mobile phase: dichloromethane/2 N ammonia in methanol=20/1, isocratic)
Quellen und Nachweise
- ORD-Eintrag
- ord-cca3bdc92ee940e8822ba1fd2d0d0e7b
- Quelldatensatz
- uspto-grants-2015_09
- Patentnummer
- US09126998B2
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