TCMDC_ArylPyrrole

See also Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride in acidic conditions (AEW 12-1)

Procedure:

PMY 2-5 (50 mg, 0.23 mmol, 1 equiv) was dissolved in anhydrous MeOH (2 mL) and AcOH (0.06 mL) was added. Pyrrolidine (22 mg, 0.025 mL, 0.3 mmol, 1.3 equiv) in anhydrous MeOH (0.5 mL) was added and the reaction mixture stirred at room temperature for 1h. Sodium cyanoborohydride (16 mg, 0.26 mmol, 1.1 equiv.) was added in two portions over two minutes and the reaction mixture stirred at room temperature for 12 h. MeOH removed in vacuo and then basified by the addition of a 1M aqueous solution of NaOH. Extracted with DCM (2 x 10 mL) and organic layers washed with brine, dried and evaporated to yield an orange oil that decomposed on the column.

Hazard and Risk Assessment:

See Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride in acidic conditions (AEW 12-1)