Tetrahydrofuran → 3-Aminomethyl-1-benzhydrylazetidine

Reaction equation

[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][CH:10]([C:12]#[N:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(O)C>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][CH:10]([CH2:12][NH2:13])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Procedure

A solution of 10.0 g (40 mmol) 1-diphenylmethyl-azetidin-3-carbonitrile in 20 ml abs. THF is added dropwise to a suspension of 3.1 g (80 mmol) lithium aluminium hydride in 80 ml abs. THF at RT and stirred overnight. The batch is carefully added to 2 ml ethanol and filtered. The filtrate is concentrated under vacuum and dispersed between CHCl3 and water. The aqueous phase is extracted twice, each with 50 ml CHCl3, and the combined organic phases are dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3CH3OH/NH4OH (90/10/0 to 90/10/1). Yield: 5.6 g (55%) of slowly hardening resin.