Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2007-05-22
2007-05-22
Parsa, J. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S467000, C544S178000, C548S579000
Reexamination Certificate
active
11040762
ABSTRACT:
The present invention relates to a method comprising the step of contacting under hydroaminomethylation conditions, an olefin, an amine, a rhodium-phosphorous ligand, and synthesis gas (syngas). In particular, it has been discovered that, under some circumstances, a neutral rhodium-monodentate phosphite ligand is prescribed. The invention provides a simple way of making, in high yields and regiospecificity, a variety of products, including pharmacologically active products such as ibutilide, terfenadine, and fexofenadine, and derivatives thereof.
REFERENCES:
patent: 3513200 (1970-05-01), Biale
patent: 4748261 (1988-05-01), Billig et al.
patent: 103 21 421 (2003-05-01), None
patent: 1 468 773 (1974-07-01), None
patent: WO 96/02508 (1996-02-01), None
patent: WO 01/64621 (2001-09-01), None
Breit B., “Substrate-Directed Diastereoselective Hydroaminomethylation of Methallyilic Alcohols,” Tetrahedron Letters, vol. 39, No. 29, pp. 5163-5166, 1998.
Rische et al., “One-Pot Synthesis of Pharmacologically Active Secondary and Tertiary 1-(3,3-Diarylpropyl)amines via Rhodium-Catalysed Hydroaminomethylation of 1,1-Diarylethenes”, Tetrahedron, vol. 55, No. 7, pp. 1915-1920, 1999.
Lin, et al., “Zwitterionic rhodium complex catalzyed hydroaminomethylation of arylethylenes,” Tetrahedron Letters, vol. 42, No. 13, pp. 2423-2425, 2001.
Teuma et al., “Tandem Carbonylation Reactions: HYdrolomylation aand Hydroeaminomethylation of alkenes catalyzed by cationic A(H2C(3,5-ME2PZ)2)Rh(CO)LU+Complexes,” Organometallics, vol. 22, No. 25, pp. 5261-5267, 2003.
Rische et al., “One-Pot Synthesis of Secondary and Tertiary Napthpropylamines by Rhodium(I)-Catalysed Carbonlative Hydroaminomethylation,” Tetrahedron, vol. 55, No. 25, pp. 7841-7846, 1999.
Nagy et al., “Homogeneous catalytic hydroaminomethlatio not steroids with aminoalcohols,” Journal of Organometallic Chemistry, vol. 586, No. 1, pp. 101-105, 1999, date unknown.
Liebigs Ann. Chem. 1953, 582, 133-161.
Jones, J. Organomet. Chem. 1989, 366, 403-408.
Tetrahedronl, 1999, 55, 9801-9816.
Beller et al., J. Am. Chem. Soc., 2003, 125, 10311-13018.
Science, 2002, 297, 1676-1678, Seayad et al.
Pruett, J. Org. Chem., 1969, 34, 327.
Van Leeuwen et al., Organometallics, 1995, 14, 34-43.
J. Am. Chem. Soc., 1993, 115, 2066-2068.
Bergmann et al., Tetrahedron, Lett., 1997, 38, 4315-4318.
Angew. Chem. Int. Ed., 2003, 42, 5615-5619.
Gupta, P., P. Tet. Lett., 2003, 44, 4231-4232.
Morita, et al., Tetrahedron 1998, 54, 4811.
Briggs John R.
Klosin Jerzy
Whiteker Gregory T.
Dow Global Technologies Inc.
Parsa J.
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