Electrochemical production of sterically hindered amines

Details Electrochemical production of sterically hindered amines Electrochemical production of sterically hindered amines

C - Chemistry, Metallurgy

25

B

C25B 3/04 (2006.01) C07C 209/30 (2006.01)

Patent

CA 2655862

The invention relates to a method for producing an amine, comprising the step of cathodic reduction of a corresponding oxime derivative of general formula (I), wherein R represents C1-6 alkyl or C2-6 alkenyl, which is optionally substituted with one or more substituents independently selected from the group consisting of phenyl, O-C1-6 alkyl, NH-C1-6 alkyl, N(C1-6 alkyl)2, OH and NH2; R1 represents H; C1-6 alkyl or C(O)-C1-6 alkyl and A represents a 5-, 6- or 7-membered hydrocarbon ring which is saturated or which has a double bond and wherein optionally at least one CH2 group is replaced by -O-, -S- -NH-, -N=, or -N(C1-6 alkyl)- and which is optionally substituted with one or more other substituents independently selected from the group consisting of phenyl, C1-6 alkyl, O-C1-6 alkyl, NH-C1-6-alkyl, N(C1-6 alkyl)2, OH and NH2; and the oxime derivative, with respect to the carbon ring having the substituent R, having an excess of the R or S form of at least 10 %.

L'invention concerne un procédé de fabrication d'une amine comportant une étape de réduction cathodique d'un dérivé d'oxime correspondant, représenté par la formule (I), dans laquelle R est C1-6-alkyle ou C2-6-alcényle éventuellement substitué avec un ou plusieurs substituants choisis indépendamment dans le groupe comportant phényle, O-C1-6-alkyle, NH-C1-6-alkyle, N(C1-6-alkyle)2, OH et NH2; R1 est H, C1-6-alkyle ou C(O)-C1-6-alkyle; et A est un cycle hydrocarbure à 5, 6 ou 7 éléments, saturé ou présentant une double liaison, sur lequel au moins un groupe CH2 est remplacé par -O-, -S- -NH-, -N=, ou -N(C1-6-alkyle), et éventuellement substitué avec un ou plusieurs autres substituants choisis indépendamment dans le groupe comportant phényle, C1-6-alkyle, O-C1-6-alkyle, NH-C1-6-alkyle, N(C1-6-alkyle)2, OH et NH2. Par rapport au cycle hydrocarbure présentant le substituant R, le dérivé d'oxime présente un excès d'au moins 10 % de la forme R ou S.

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