Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1993-07-08
1995-02-21
Richter, Johann
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540557, 544336, 544242, 544256, 546329, 546176, 546139, 548561, 5483355, 5483097, 548254, 5483751, 548491, 548482, 548444, 548247, 548152, 548224, 548202, 548235, 549491, 549 74, 549467, 549 49, 549 23, 552 10, C07D30702, C07C24700
Patent
active
053917723
ABSTRACT:
Described is a process for converting an alcohol to an azide with S.sub.N 2 inversion using a phosphoryl azide, e.g. diphenylphosphoryl azide (DPPA). Good yields of azide in high enantiomeric excess can be achieved specifically for benzylic alcohols and alpha-hydroxy alkyl esters. The process is carried at preferably room temperature in an inert dry aprotic solvent, e.g. toluene, and in the presence of a proton acceptor, e.g. 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) to afford high yields of high enantiomeric purities.
REFERENCES:
patent: 5157129 (1992-10-01), Blacklock et al.
J. Med. Chem. 1992, 35, 3745.
J. Am. Soc. 1972, 94, 679, by Mitsunobu, et al.
Org. React. 1992, 42, 335, by D. L. Hughes.
Tetrahedron Letter, 1991, 32, 7175, by C. Chen, et al.
Tetrahedron Letter, 1977, 23, 1977 by B. Lal, et al.
Synthesis, 1990, 130, by M. C. Viaud, et al.
J. Am. Chem. Soc., 1992, 114, 2741, by C. M. Gasparski.
J. Org. Chem. 1993, 58, 1672, by T. J. Blacklock, et al.
Angew. Chem. Int. Ed. Engl. 1983, 22, 65 by F. Effenberger, et al.
Synthesis 1987, 190, by E. Fabiano, et al.
Tetrahedron 1992, 48, 3007, by R. V. Hoffman.
J. Org. Chem. 1981, 46, 5173, by J. Zaloom, et al.
Fieser and Fieser's Reagents for Organic Synthesis, vol. 8, p. 211, by Mary Fieser, 1980.
Tetrahedron Letters, vol. 30, No. 42, pp. 5709-5712, 1989, by J. R. Henry, et al.
Tetrahedron Letters, vol. 31, No. 24, pp. 3417-3420, 1990, by M. L. Edwards, et al.
J. of Amer. Chem. Society, 97:24, Nov. 26, 1975, by M. Tachikawa, et al.
Biochemistry 1992, 31, 8160-8170, W. B. Knight, et al.
Tetrahedron Letters, 1657, 30, 1989.
Tetrahedron Letters, 7095, 30, 1989.
Grabowski Edward J. J.
Thompson Andrew S.
Cook Rebecca
Merck & Co. , Inc.
North Robert J.
Panzer Curtis C.
Richter Johann
LandOfFree
Converting an alcohol to an azide with S.sub.N 2 inversion using does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Converting an alcohol to an azide with S.sub.N 2 inversion using, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Converting an alcohol to an azide with S.sub.N 2 inversion using will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1931552