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29th October 2012 @ 03:29
Reaction Scheme

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, (N.B should be complete after 16 h or less, left for longer due to unforseen circumstances) TLC indicated two products (presumably products from reductive amination at both nitrogen atoms 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.

TLC (5% MeOH in DCM) after 40 hours, UV then vanillin:
AEW 19-1 reaction mixture is second spot from the left
AEW 19 and 2_1, vanillin.png
AEW 19and20_1 UV.jpg


1H NMR Data:
AEW 19-1 col.zip
AEW 19-1 Col.pdf
aew19-1 crude.zip
AEW 19-1 crude.pdf
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