HYDROGENATION OF IMINES Russian patent published in 2013 - IPC C07C215/68 C07C213/08 C07C233/07 C07C233/54 B01J23/40 

FIELD: chemistry.

SUBSTANCE: present invention relates to an improved method for asymmetric hydrogenation of an imine of formula 1 with hydrogen at high pressure in the presence of a catalyst system to obtain an amine of formula 2.

. Said catalyst system includes a ligand which forms a complex with a metal selected from iridium and rhodium or salts thereof. Said ligand is selected from a group comprising: a.[(1R,2R,3S)-1,2-dimethyl-2,3-bis(diphenylphosphinomethyl)-cyclopentyl]methanol; b. (1S,4S,11R)-1,11-bis-[(diphenylphosphanyl)-methyl]-11-methyl-1,2,3,4-tetrahydro-1,4-methano-phenazine; c.(R)-3-di-(3,5-dimethylphenyl)phosphino-2-(4-diphenylphosphino-2,5-dimethylthienyl-3)-1,7,7-trimethylbicyclo-[2,2,1]-hept-2-ene; d. (S)-2-[(o-diphenylphosphino)-phenyl]-1-diphenylphosphino-ferrocene; e. (S)-1-(diphenylphosphino)-2-(S)-(o-diphenylphosphino-α-methoxybenzyl)ferrocene; f. (+)-(S)-N,N-dimethyl-1-[(R)-1',2-bis-(diphenylphosphino)-ferrocenyl]-ethylamine; and g. [(S)-)-[(R)-2-diphenylphosphino)ferrocenyl]-ethyl-di(cyclohexyl)-phosphine. The process can be carried out in the presence of an additive selected from a group comprising diadamantyl butyl phosphonium hydroiodide (A), diadamantyl benzyl phosphonium hydrobromide (B), triphenyl phosphonium diiodide (C), isopropyl triphenyl phosphonium iodide (D), triphenyl phosphonium dibromide (E), methyl triphenyl phosphonium bromide (F), tetrabutyl ammonium iodide (G), copper (II) triflate (H) and ytterbium (II) triflate (I), triphenyl phosphonium dichloride (J), in an inert organic solvent selected from a group comprising toluene, 1,4-dioxane methanol, tetrahydrofuran, dichloromethane. The obtained amine of formula 2 is optionally reacted with chloroacetyl chloride to obtain a compound 3. Compound 3 is used as a herbicide.

EFFECT: method avoids the need for high-corrosion special equipment while simultaneously achieving high enantioselectivity and degree of conversion of the raw product.

11 cl, 8 tbl, 18 ex