Process for the preparation of an alpha-amino carbonyl compound
OwnerDavid Hyett, Daniel Mink +3inventors
InventorsDavid Hyett, Daniel Mink, Quirinus Broxterman, Bernardus Kaptein, Hubertus Zeegers
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Abstract
The invention relates to a process for the preparation of an α-amino carbonyl compound by reacting an imine starting material with a suitable electrophile in the presence of a base. This process has the advantage that the imine starting materials can be prepared from glyoxylic acid esters or glyoxylic acid ester derivatives and α-hydrogen containing primary amines, which are usually cheap and readily available. These imine starting materials can usually be prepared with a high yield and/or almost without the formation of any side products.
Claims24
Process for the preparation of an (x-amino-carbonyl compound of formula 1,
- wherein R1 and R2 each independently stand for optionally substituted (cyclo)alkyl, optionally substituted (cyclo)alkenyl, optionally substituted (hetero)aryl, CN or C(O)R6, —wherein R6 stands for OR12—, —wherein R12 stands for an optionally substituted (cyclo)alkyl, an optionally substituted aryl- or wherein R6 stands for NR13R14, —wherein R13 and R14 are each independently chosen from the group of H, optionally substituted (cyclo)alkyl and optionally substituted (hetero)aryl and wherein R13 and R14 may form a ring together with the N-atom to which they are connected- and wherein R1 and/or R2 may be part of a ring system formed by a connection between R1 and R2, between R1 and E, between R2 and E, between R1 and X or between R2 and X, wherein X and E are as defined below,
- wherein E stands for H, an optionally substituted (cyclo)alkyl, a halogen, a tri-substituted silyl group, an optionally substituted (cyclo)alkenyl, an optionally substituted (hetero)aryl or wherein E stands for C(O)R40, —wherein R40 stands for H, an optionally substituted (cyclo)alkyl, an optionally substituted (hetero)aryl or for OR41, —wherein R41 stands for an optionally substituted (cyclo)alkyl or an optionally substituted (hetero)aryl or wherein R40 stands for NHR42, —wherein R42 stands for H, an optionally substituted (cyclo)alkyl or for an optionally substituted aryl-,
- and wherein X stands for OR5, —wherein R5 stands for an optionally substituted (cyclo)alkyl, an optionally substituted aryl- or wherein X stands for NR3R4, —wherein R3 and R4 each independently stand for H, an optionally substituted (cyclo)alkyl or an optionally substituted (hetero)aryl and wherein R3 and R4 may form a ring together with the N-atom to which they are bound-,
- and wherein X together with E may form part of a lactone or lactam ring system together with the C-atoms to which they are bound, characterized in that an imine of formula 2,
- wherein R1, R2 and X are as defined above, is reacted with a suitable electrophile in the presence of a base to form the corresponding a-amino carbonyl compound of formula 1.
Dependencies are inferred from the claim text.