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6th June 2013 @ 12:59

See also:Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride in acidic conditions (AEW 9-2)

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. 4-Amino-1-benzylpiperidine (61 mg, 0.30 mmol) 2.6 equiv of this liquid added in error 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 18 h. Then volatiles removed in vacuo and NaOH 1M aqueous was added and the mixture extracted into DCM (x2). Combined organics were washed with brine, dried over MgSO4, filtered and evaporated to yield a dark yellow/orange oil (133 mg).

 

Crude NMR:

AEW 9-3.zip

Hazard and Risk Assessment:

See Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride in acidic conditions (AEW 9-2)

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AEW 9-3.zip