Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1996-04-19
1997-05-27
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C07C23322
Patent
active
056334044
ABSTRACT:
A method of making ( R)- N-[1-(3-methoxyphenyl)ethyl]-3-(2-chlorobenzene)propanamine which involves reducing the appropriate amidyl or iminyl precursor with an appropriate reducing agent. The appropriate amidyl or iminyl precursor is made from a synthesis involving the use of ( R)-3-methoxy-.alpha.-methylbenzylamine. A method of condensing a nitrile with a primary or secondary amine to form an imine involves the reaction of a nitrile with diisobutylaluminum hydride; and then reacting the resultant compound with a primary or secondary amine to form the imine. The process is especially useful for producing enantiomerically pure chiral imines, and, ultimately, amines. Typical such imines have the formula: ##STR1## wherein R, R.sub.1, R.sub.2 and R.sub.3 are independently selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, aryl and aralkyl.
REFERENCES:
patent: 2798094 (1957-07-01), Shepard et al.
patent: 4024274 (1977-05-01), Druckrey et al.
patent: 4925664 (1990-05-01), Jackson et al.
patent: 5064657 (1991-11-01), Jackson et al.
patent: 5300437 (1994-04-01), Stirling et al.
patent: 5326784 (1994-07-01), Junien et al.
#"ASN Program & Abstracts", Journ. Am. Soc. Neph., vol. 4, No. 3, 120P, 69P, p. 719, Sep., 1993.
#Barnes et al., "The Use of 4-Substituted Hydrindenes in the Preparation of Cyclopentanophenanthrene Derivatives", Journ. Am. Chem. Soc., vol. 71, pp. 2644-2647, Aug., 1949.
#Barney et al., "A Convenient Synthesis Of Hindered Amines And .alpha.-Triluoromethylamines From Ketones", Tetrahedron Letters vol. 31, No. 39, pp. 5547-5550, 1990.
#J. Brussee et al., "Synthesis Of Optically Active Ethanolamines", Tetrahedron, vol. 46, No. 5, pp. 1653-1658, 1990.
#Chemical Abstracts, 99:104949b, 1983, vol. 99, pp. 558.
#Chemical Abstracts, 116:128255t, 1992, vol. 116, p. 823.
#1993 Program & Abstracts, Journal of Bone and Mineral Research, vol. 8, Supplement 1, pp. S175, S181, Aug., 1993.
#Jasys et al., "The Total Synthesis Of Argiotoxins 636, 659 And 673", Tetrahedron Letters, vol. 29, No. 48, pp. 6223-6226, 1988.
#Mattson et al., "An Improved Method for Reductive Alkylation of Amines Using Titanium (IV) Isopropoxide and Sodium Cyanoborohydride", J. Org. Chem., vol. 55, No. 8, pp. 2552-2554, 1990.
#Marino et al., "An Improved Synthesis of 3-Methyl-5-Hydroxy Protected Indoles", Synthetic Communications,24(6), pp. 839-848, Mar. 1994.
#Nason et al., "Synthesis of Neurotoxic Nephila Spider Venoms: NSTX-3 and JSTX-3", Tetrahedron Letters, vol. 30, No. 18, pp. 2337-2340, 1989.
#Sheldon, Roger A., "The Industrial Synthesis Of Pure Enantiomers", Drug Information Journal, vol. 24, pp. 129-139, 1990.
#P. Zandbergen et al., "A One-Pot Reduction-Transimination-Reduction Synthesis of N-substituted .beta.-Ethanolamines from Cyanohydrins.", Tetrahedron, vol. 48, No. 19, pp. 3977-3982, 1992.
Duff Steven R.
Nelson William A.
VanWagenen Bradford C.
NPS Pharmaceuticals Inc.
Raymond Richard L.
LandOfFree
N-((R)-.alpha.-methyl-3-methoxybenzyl)-3-(2-chlorobenzene)propan does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with N-((R)-.alpha.-methyl-3-methoxybenzyl)-3-(2-chlorobenzene)propan, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N-((R)-.alpha.-methyl-3-methoxybenzyl)-3-(2-chlorobenzene)propan will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2330430