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27th September 2012 @ 06:31
Reaction Scheme

Incomplete conversion of starting material after 27 hours reaction time. Trace amounts of product visible by UV, visualised by vanillin. Alternative method using sodium cyanoborohydride will be explored in AEW 9-2

PMY 2-5 (70 mg, 0.32 mmol, 1.1 equiv.) was stirred in anhydrous DCM (4.5 mL). 4-amino-1-benzylpiperidine (86 mg, 0.42 mmol, 1.3 equiv.) in DCM (1 mL) was added followed by freshly activated molecular sieves. The reaction mixture was stirred for 5 minutes at room temperature. Sodium triacetoxyborohydride (89 mg, 0.42 mmol, 1.3 equiv.) was added and the reaction left to stir at room temperature. After 2 hours, no conversion was observed by TLC. After 24 hours, still lots of starting material, one spot on the baseline (corresponding to the starting amine), not visible by UV, could be partially visualised with vanillin. Reaction not taken further Paul Ylioja suggested a method using sodium cyanoborohydride that had been effective in reductive amination of the same parent aldehyde See: Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium cyanoborohydride in acidic conditions (PMY 38-5)

TLC (25% EtoAc in Hexane) visualised with UV and vanillin:
AEW 9-1.jpg

NB please ignore other TLC photo, this was uploaded in error

Risk and Hazard Assessment:
AEW 9-1 HIRAC.pdf


See also:
Synthesis of amine-linked analogue of TCMDC-123812 via reductive amination using sodium triacetoxyborohydride (PMY 38-2)

Reference:
doi:10.1021/jo960057x
Linked Entries
Attached Files
AEW 9-1.png
AEW 9-1 vanillin.jpg
AEW 9-1.jpg
AEW 9-1 HIRAC.pdf
AEW 9-1.png
Comments
Re: Reductive Amination (AEW 9-1) by OSDD Malaria
25th January 2014 @ 12:06
OSM-S-95