Process for producing and method of crystallizing 2-azabicyclo[2

Details Process for producing and method of crystallizing 2-azabicyclo[2 Process for producing and method of crystallizing 2-azabicyclo[2

1998-12-28

2000-05-09

McKane, Joseph

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D20952

Patent

active

060606096

ABSTRACT:
A process for producing 2-azabicyclo[2.2.1]hept-5-en-3-one is provided by reacting a sulfonyl cyanide represented by the general formula R-SO.sub.2 CN (in which R represents an alkyl group or a phenyl group which may have a substituent), in the presence of water and in a hydrocarbon solvent at a pH of 4 to 7 inclusive. 2-Azabicyclo[2.2.1]hept-5-en-3-one can be produced in a high yield and a high purity in one step process, with a reduced amount of solvent used, safely and with good productivity. A method of crystallizing 2-azabicyclo[2.2.1]hept-5-en-3-one is also provided, which includes dissolving 2-azabicyclo[2.2.1]hept-5-en-3-one into an organic solvent mainly including at least one of diisopropyl ether and methyl tertiary butyl ether, cooling the solution to deposit crystals of 2-azabicyclo[2.2.1]hept-5-en-3-one. Finely divided particulate crystals of 2-azabicyclo[2.2.1]hept-5-en-3-one excellent in fluidity and handleability can be obtained with a simple procedure and in a high recovery rate.

REFERENCES:
patent: 5200527 (1993-04-01), Griffiths et al.
patent: 5300649 (1994-04-01), Griffiths et al.
patent: 5847157 (1998-12-01), Romanowski et al.
Chemical Abstracts, AN 316997, vol. 124, No. 23, Jun. 3, 1996, JP 8-027110, Jan. 30, 1996.
Chemical Abstracts, AN108526, vol. 121, No. 09, Aug. 29, 1994, JP 05 331140, Dec. 14, 1993.
J. Org. Chem., 1985, vol. 50, 1983-1985, An Approach to the Synthesis of Neplanocin A, William C. Faith et al.
J. Org. Chem., 1993, vol. 58, 6129-6131, Diels-Alder Reaction of Methanesulfonyl Cyanide with Cyclopentadiene. Industrial Synthesis of 2-Azabicyclo[2.2.1]Hept-5-En-3-One, Gareth J. Griffiths, et al.
Chem. Pharm. Bull., vol. 44, 1996, 850-852, Hetero Diels-Alder Reaction of Benzenesulfonyl Cyanide With Cyclopentadiene Using Chiral Lewis Acids, Nobuya Katagiri et al.
J. Org. Chem., vol. 39, No. 4, 1974, 564-566, Diels-Alder Cycloadditions of Sulfonyl Cyanides with Cyclopentadiene. Synthesis of 2-Azabicyclo[2.2.1]Hepta-2,5-Dienes, J. C. Jagt et al.
J. Org. Chem., vol., 43, No. 12, 1978, 2311-2320, Synthesis of Carbocyclic Aminonucleosides, Susan Daluge et al.
J. Org. Chem., vol. 46, 1981, 3268-3272, Carbocyclic Sugar Amines: Synthesis and Stereochemistry of Racemic .alpha.- and B-Carbocyclic Ribofuranosylamine, Carbocyclic Lysofuranosylamine, and Related Compounds, Bernard L. Kam, et al.
J.C.S. Perkin I, 874-884, Reaction of Chlorosulphonyl Isocyanate With 1,3-Dienes. Control of 1,2- and 1,4-Addition Pathways and the Synthesis of Aza- and Oxa-Bicyclic Systems, J.R. Malpass, et al., Jul. 1976.

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