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29th October 2012 @ 03:29
PMY 2-5 (200 mg, 0.92 mmol, 1 equiv.) was dissolved in anhydrous MeOH (10 mL) and AcOH (0.24 mL) was added. 4-Aminopiperidine (97 μL, 0.92 mmol, 1 equiv.) was added and the reaction mixture stirred at room temperature for 2 h. Sodium cyanoborohydride (64 mg, 1.01 mmol, 1.1 equiv.) was added in two portions over two minutes and the reaction mixture stirred at room temperature for 40 hours, [i](N.B should be complete after 16 h or less, left for longer due to unforseen circumstances)[/i] TLC indicated two products [i](presumably products from reductive amination at both nitrogen atoms[/i] Methanol removed in vacuo and then the crude orange oil treated with 1M NaOH (10 mL). The mixture was then extracted with DCM (2 x 20 mL). The organic extracts were washed with brine then dried (MgSO4) and concentrated to give an orange oil. [b]TLC (5% MeOH in DCM) after 40 hours, UV then vanillin:[/b] [i]AEW 19-1 reaction mixture is second spot from the left[/i] [data]3678[/data][data]3676[/data] [b]1H NMR Data:[/b] [data]4196[/data][data]4194[/data][data]4192[/data][data]4190[/data]
Attached Files
AEW 19and20_1 UV.jpg
AEW 19 and 2_1, vanillin.png
AEW 19-1.png
AEW 19-1 crude.pdf
aew19-1 crude.zip
AEW 19-1 Col.pdf
AEW 19-1 col.zip