Potassium Sodium Tartrate → 2-((2RS,3SR)-2,3-Diethylazetidin-1-yl)ethanamine Hydrochloride

Participants

Reaction Steps

AlCl3 (3.37 g, 25.3 mmol) in dry ether (140 ml) was added to a stirred suspension of 1M LAlH4 in ether (25.3 ml, 25.3 mmol) in ether (140 ml). The mixture was heated at reflux for 30 mins and after cooling to RT the mixture was transferred by cannula into a solution of 2-((2RS,3RS)-2,3-diethyl-4-oxoazetidin-1-yl)acetonitrile (step 3) (1.4 g, 8.42 mmol) in dry ether (50 ml). Stirring was continued at RT for 16 hrs. The reaction mixture was cooled to 0° C. and Rochelle salt (aq 50 ml) was added. The mixture was allowed to stir at RT for 24 hr. The aqueous was separated and the ether layer was retained. The aqueous was stirred with 10% trifluoroethanol/DCM (250 ml) for 3 hrs then the layers were separated and the aqueous was further stirred with 10% trifluoroethanol/DCM {250 ml} for a further 2 hrs. The remaining aqueous was extracted with 10% trifluoroethanol/DCM (×3). The combined organic layers were treated with 1M HCl in methanol and concentrated in vacuo to afford the title compound;

Provenance & Evidence