I am looking for methods that can give maximum conversion of ketone and aminoacid hydrochloride to ketimine, specifically ethyl glycinate.HCl and methyl N-acetyl lysinate.HCl. Any kind of suggestion will be highly appreciated.
Firts of all system TiCl4/Et3N.
You used DIPEA in 1eq., freebase glycine ester could dimerize into pyperazinedion. Or you added DIPEA by steps?
Try using Ce(III) neutral pH catalyst - for inspiration see
https://www.researchgate.net/publication/276059289_Kabachnik-Fields_and_Prins-Ritter_Synthesis_Application_of_CeIII_Supported_on_a_Weakly_Acidic_Cation-exchanger_Resin_in_Comparative_Study
https://www.researchgate.net/publication/267390365_Comparative_Studies_of_Catalytic_Application_of_CeriumIII_Chloride_and_Resin_Supported_CeriumIII_in_Domino_Syntheses_of_15-Benzodiazepine_and_13-Diazine_Skeletons
https://www.researchgate.net/publication/265959505_Synergism_of_Metal_and_Organocatalysis_in_Condensation_Reactions_of_Aromatic_Aldehydes_with_Anilines_Affording_Imines_Effect_of_Catalysts_on_the_Base_of_a_Supported_CeriumIII_and_Proline
Article Kabachnik-Fields and Prins-Ritter Synthesis: Application of ...
Article Comparative Studies of Catalytic Application of Cerium(III) ...
Article Synergism of Metal and Organocatalysis in Condensation React...
Dear Syeda Aaliya Shehzadi
I agree with the answers of Jesse DuPont and Pavel Pazdera.
Good luck
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