All Notebooks | Help | Support | About
24th October 2012 @ 03:14
[i]Repeated as purification of AEW 11-1 was problematic, this time 1:1 aldehyde:amine used to prevent problems of separating excess piperidine[/i] 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 (45 μL, 0.46 mmol, 1 equiv.) in anhydrous MeOH (1 mL) was added and the reaction mixture stirred at room temperature for 1h. Sodium cyanoborohydride (32 mg, 0.51 mmol, 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 [i]in vacuo[/i] 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. [b]TLC (5% MeOH in DCM) after hours, UV then vanillin:[/b]