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3rd October 2012 @ 08:29
Reaction Scheme

PMY 2-5 (100 mg, 0.46 mmol, 1 equiv.) was dissolved in anhydrous MeOH (4 mL) and AcOH (0.12 mL) was added. Piperidine (51 mg, 0.60 mmol, 1.3 equiv.) in anhydrous MeOH (1 mL) was added and the reaction mixture stirred at room temperature for 1h. Sodium cyanoborohydride (32 mg, 0.51 mmil, 1.1 equiv.) was added in two portions over two minutes and the reaction mixture stirred at room temperature for 16 hours. TLC indicated product, SM (AEW 2-1) and a spot above the SM. Reaction was stopped to prevent formation of further side products: Methanol removed in vacuo and then the crude orange oil treated with 1M NaOH (5 mL). The mixture was then extracted with DCM (2 x 10 mL). The organic extracts were washed with brine then dried (MgSO4) and concentrated to give an orange oil.

TLC (5% MeOH in DCM) after 16 hours, UV then vanillin:

AEW 11-1 and 12-1 16 h vanillin.jpg
AEW 11-1 and 12-1 16 h.jpg


second spot from left corresponds to AEW 11-1, second spot from right corresponds to AEW 12-1
Attached Files
AEW 11-1.png
AEW 11-1.png