Patent ID: 8716524
Filing Date: 2014-05-06
Classification: B01J,C07C,C07D

Abstract:
1. A method for producing an optically active α-amino acid, comprising: alkylating a compound represented by the formula (IV): with a compound of the formula (V): to give a compound represented by the formula (VI): using a compound represented by the formula (I) that is pure with respect to axis symmetry as a phase-transfer catalyst: in a medium in the presence of an inorganic base, wherein in the formula (I), R 1 , R 1′ , R 2 , R 2′ , R 3 , R 3′ , R 4 , R 4′ , R 5 , R 5′ , R 6 , and R 6′ are groups independently selected from the group consisting of: (i) a hydrogen atom; (ii) —NR (iii) a cyano group; (iv) a nitro group; (v) a carbamoyl group; (vi) an N—(C (vii) an N,N-di(C (viii) —NHCOR (ix) a C (x) a C (xi) a C (xii) an aralkyl group, wherein the aryl moiety of the aralkyl group may be substituted with at least one group selected from the group consisting of: a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; (xiii) a heteroaralkyl group having a heteroaryl moiety, wherein the heteroaryl moiety may be substituted with at least one group selected from the group consisting of: a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; (xiv) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of: a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom, and —S—R, —SO—R, or —SO or may be substituted with —O—CH 2 —O— or —O—(CH 2 ) 2 —O— at positions 3 and 4 taken together; and (xv) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of: a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; and R 7 and R 8 are groups independently selected from the group consisting of: (i) a hydrogen atom; (ii) a C (iii) a C (iv) a C (vii) —(CH and n is an integer from 1 to 12); (viii) —(CH and n is an integer from 1 to 12); (ix) —(CH and n is an integer from 1 to 12); (x) —(CH and n is an integer from 1 to 12); (xi) —(CH and n is an integer from 1 to 12); (xii) —(CH and n is an integer from 1 to 12); (xiii) —(CH and n is an integer from 1 to 12); (xiv) —(CH and n is an integer from 1 to 12); and (xv) —(CH and n is an integer from 1 to 12); or R 7 and R 8 are taken together to form a divalent group selected from the group consisting of: —(CH 2 ) m — (where m is an integer from 2 to 8); wherein X − is an anion selected from the group consisting of a halide anion, SCN − , HSO 4 − and HF 2 − , provided that in a case where R further provided that in a case where R 1 , R 1′ , R 2 , R 2′ , R 3 , R 3′ , R 4 , R 4′ , R 5 , R 5′ , R 6 , and R 6′ are all hydrogen atoms and X − is a bromide ion or an iodide ion, R 7 and R 8 are not both cyclohexyl groups or allyl groups, in the formulae (IV) and (VI), R 14 and R 15 are each independently (i) a hydrogen atom; or (ii) an aryl group that may be substituted with a C with the proviso the case where both R R 16 is a group selected from the group consisting of: (i) a hydrogen atom; (ii) a C (iii) a C (iv) a C (v) an aralkyl group, wherein the aryl group of the aralkyl group may be substituted with at least one group selected from the group consisting of: a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; (vi) a heteroaralkyl group having a heteroaryl moiety, wherein the heteroaryl moiety may be substituted with at least one group selected from the group consisting of: a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; (vii) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of: a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; and (viii) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of: a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; R 17 is a C 1 to C 8 alkyl group that may be branched or form a cyclic group), in the formulae (V) and (VI), R 18 is a group selected from the group consisting of: (i) a C (ii) a C (iii) a C (iv) a C (v) an aralkyl group, wherein the aryl moiety of the aralkyl group may be substituted with at least one group selected from the group consisting of; a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; (vi) a heteroaralkyl group having a heteroaryl moiety, wherein the heteroaryl moiety may be substituted with at least one group selected from the group a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; (vii) an aryl group, wherein the aryl group may be substituted with at least one group selected from the group consisting of; a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; (viii) a heteroaryl group, wherein the heteroaryl group may be substituted with at least one group selected from the group consisting of: a C a C an aryl group that may be substituted with a C a cyano group, —NR a nitro group, a carbamoyl group, an N—(C an N,N-di(C —NHCOR a halogen atom; and (ix) a C in the formula (V), W is a functional group having a leaving ability, and in the formula (VI), * shows a newly produced asymmetric center; and hydrolyzing an imino group (R under an acidic condition.