Aluminium lithium hydride → (S)-(1-benzylpiperidin-2-yl)methanol
Reaktionsgleichung
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O>O1CCCC1>[CH2:17]([N:12]1[CH2:13][CH2:14][CH2:15][CH2:16][C@H:11]1[CH2:9][OH:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Lithium aluminum hydride was added to an ice-cooled solution of (2S)-1-benzylpiperidine-2-carboxylic acid methyl ester (178 mg) in tetrahydrofuran (2.7 ml) under nitrogen atmosphere. The mixture was stirred for 2 hours below 5° C. The reaction was quenched by a sequential addition of water (0.12 ml), 15% aqueous sodium hydroxide (0.12 ml) and water (0.36 ml) successively, and the whole was stirred at room temperature for 1 hour. The insoluble materials were removed by filtration. The filtrate was dried over sodium sulfate and evaporated under reduced pressure to give (2S)-1-benzyl-2-(hydroxymethyl)piperidine as a colorless oil.