Aluminium lithium hydride → Tert-butyl 4-(hydroxymethyl)-4-[(2-methylphenyl)methyl]piperidine-1-carboxylate
Reaktionsgleichung
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:14][C:15](=O)[C:16]1([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)C1C=CC=CC=1>CCOCC>[C:25]([O:24][C:22]([N:19]1[CH2:18][CH2:17][C:16]([CH2:15][OH:14])([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[CH3:36])[CH2:21][CH2:20]1)=[O:23])([CH3:27])([CH3:28])[CH3:26]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a suspension of lithium aluminum hydride (0.32 g, 8.4 L s mmol) in anhydrous ether (50 ml) was added a solution of 4-(2-methylbenzyl) N-t-butoxycarbonyl isonipecotic acid benzyl ester (3.0 g, 7.1 mmol) in anhydrous ether (25 ml) over 15 min. The resulting mixture was heated gently at reflux for 1 h. The reaction mixture was then quenched with the slow and successive addition of H2O (0.32 ml), 15% aqueous NaOH, and H2O (0.96 ml). After sirring for 30 min., the mixture was filtered through Celite and the filtrate washed with brine, dried (MgSO4), and concentrated in vacuo to a colorless syrup. Purification by column chromatography on silica with 25%-50% EtOAc/hexane as eluent afforded the product as a colorless gum. This material was recrystallized from EtOAc and hexane to afford a white solid. m.p. 104°-106° C.