What are the difficulties associated with reductive amination? One is byproduct formation. What are the other problems? How to control byproduct formation? Is there any literature available to control reductive aminations?
We have been using NaBH(AcO)3 for quite a long time for the direct protocol.
http://pubs.acs.org/doi/abs/10.1021/jo960057x
It is reliable, you can even use it for solid phase synthesis. But activated
aldehyde get reduced under those conditions. When that happens we move back
to step-wise conditions but without isolating the imine, We used that procedure
to make many diamine.
http://www.sciencedirect.com/science/article/pii/S0960894X11017835
We folllow adapted the procedure used by Phanstiel
http://pubs.acs.org/doi/pdfplus/10.1021/jm0491288
Regards
Guille
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