TCMDC_ArylPyrrole

PMY 2-5 (100 mg, 0.46 mmol, 1 equiv) was dissolved in anhydrous MeOH (4 mL) and AcOH (0.12 mL) was added. Pyrrolidine (43 mg, 0.05 mL, 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 and the absence of SM (AEW 2-1). Reaction was stopped: Methanol removed in vacuoand 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.  Flash column chromatography over silica (1–10% MeOH in CH­₂Cl­­₂) gave the desired product as an orange oil (23 mg, 0.08 mmol, 18% yield).

*readily decomposes 

1H NMR:

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

second spot from right corresponds to AEW 12-1, second spot from left corresponds to AEW 11-1