I am working on a chiral N-Boc-3-heteroarene(imidazole derivative) substituted piperidine derivative, and we observed a slight drop of optical purity after removal of the Boc in HCl/dioxane(2M).
Considering acidic condition is stable for alpha-H of EWG, what else may be the cause for this racemization?
James E Hanson
Without more details of the structure, it is hard to say. But things to consider: your 3 substituted piperidine actually has 2 stereogenic centers. N1 and C3. N1 can readily invert and may be in equilibrium between 2 forms. Removal of the Boc may alter the equilibrium.
there can be other acid catalyzed isomerizations but without the detailed structure it is hard to know if they are relevant.
0 votes
0 thanks
- Badges
- Science topic
- Similar topics
- Physical Sciences
- Materials Science
- Materials Chemistry
- Polymer Chemistry
More Rengwei Sun's questions See All
Similar questions and discussions