| US 7,592,488 B2 | ||
| Method for preparing optically active amines | ||
| Mahn-Joo Kim, Pohang (Korea, Republic of); Jaiwook Park, Pohang (Korea, Republic of); Won-Hee Kim, Daejeon (Korea, Republic of); Kiwon Han, Paju-shi (Korea, Republic of); and Yoon Kyung Choi, Gyeongsangbuk-do (Korea, Republic of) | ||
| Assigned to Postech Academy-Industry Foundation, Pohang (Korea, Republic of) | ||
| Filed on Aug. 18, 2007, as Appl. No. 11/840,935. | ||
| Claims priority of application No. 10-2007-0077733 (KR), filed on Aug. 02, 2007. | ||
| Prior Publication US 2009/0035830 A1, Feb. 05, 2009 | ||
| Int. Cl. C07C 209/62 (2006.01); C07C 209/88 (2006.01) | ||
| U.S. Cl. 564—424 [564/413; 564/414; 564/415; 564/437; 549/404] | 12 Claims |
| 1. A method of preparing a chiral amine comprising:
reacting a mixture comprising an amine compound having the following Formula 1, a metal catalyst, a biocatalyst including
a lipase, and an acyl donor compound having the following Formula 2 in an organic solvent to obtain a chiral amide compound
having the following Formula 3; and
hydrolyzing the chiral amide compound to obtain a chiral amine having the following Formula 4, wherein,
 wherein, in the above Formulae 1 to 4,
R1 and R2 are connected to each other to form a ring, or are independently selected from the group consisting of hydroxyl, nitro, amino,
azido, amidino, cyano, isocyano, cyanato, thiocyanato, hydrazino, hydrazono, carbonyl, carbamyl, thiocarbamyl, thiol, mesyl,
a substituted or unsubstituted ester, carboxyl, or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt
thereof, a substituted or unsubstituted C1-C15 alkyl, a substituted or unsubstituted C2-C16 alkenyl, a substituted or unsubstituted C2-C16 alkynyl, a substituted or unsubstituted C6-C18 aryl, a substituted or unsubstituted C7-C18 arylalkyl, a substituted or unsubstituted C1-C20 heteroalkyl, a substituted or unsubstituted C2-C20 heterocycle, a substituted or unsubstituted C3-C20 heteroarylalkyl, a substituted or unsubstituted C3-C15 cycloalkyl, a substituted or unsubstituted C3-C15 cycloalkenyl, a substituted or unsubstituted C6-C15 cycloalkynyl, a substituted or unsubstituted C3-C20 heterocycloalkyl, and combinations thereof,
R3 and R4 are independently selected from the group consisting of hydroxyl, nitro, amino, azido, amidino, cyano, isocyano, cyanato,
thiocyanato, hydrazino, hydrazono, carbonyl, carbamyl, thiocarbamyl, thiol, mesyl, a substituted or unsubstituted ester, carboxyl,
or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C1-C15 alkyl, a substituted or unsubstituted C2-C16 alkenyl, a substituted or unsubstituted C2-C16 alkynyl, a substituted or unsubstituted C6-C18 aryl, a substituted or unsubstituted C7-C18 arylalkyl, a substituted or unsubstituted C1-C20 heteroalkyl, a substituted or unsubstituted C2-C20 heterocycle, a substituted or unsubstituted C3-C20 heteroarylalkyl, a substituted or unsubstituted C3-C15 cycloalkyl, a substituted or unsubstituted C3-C15 cycloalkenyl, a substituted or unsubstituted C6-C15 cycloalkynyl, a substituted or unsubstituted C3-C20 heterocycloalkyl, and combinations thereof,
wherein R1 has a bigger steric size than R2, and the metal catalyst is palladium supported on aluminum oxyhydroxide.
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