When using sodium cyanoborohydride for reductive amination, does water in the the methanol substrate affect formation of the imine?
I’m performing the reaction at a ph of ~6 for 48hrs in MeOH and workup is consistently recovering starting material with no reaction taking place.
No reaction taking place at all ? Cyanoborohydride unlike sodium borohydride tolerates apreciable quantities of water and so reaction should happen at least to some extent.
How you analised the final product? TLC is bare minimum, some spectra should Have been done to say surely that no reaction took place.
May we know what was the solution to your problem even tho u might be doing some mad chemistry.. im still curious what factors disabled cyanoborohydride. Was that really water which affected rxn speed so much?