Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile

Details Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile

1978-07-06

1980-09-30

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07D20952

Patent

active

042254990

ABSTRACT:
3-Azabicyclo(3.1.0)hexane-2-carbonitrile, a precursor for preparing 3-azabicyclo(3.1.0)hexane-2-carboxylic acid, a plant male gametocide, is prepared by (a) treating 3-azabicyclo(3.1.0)hexane with a chlorinating agent to form 3-chloro-3-azabicyclo(3.1.0)hexane; (b) treating a solution of that compound with a strong inorganic base and a lower alkanol, to give a solution of the corresponding 3-azabicyclo(3.1.0.)hex-2-ene; (c) treating the solution with an alkali metal bisulfite to form the 2-bisulfite adduct of 3-azabicyclo(3.1.0)hex-2-ene; (d) treating the reaction mixture containing the adduct with an alkali metal cyanide to form 3-azabicyclo(3.1.0)hexane-2-carbonitrile.

REFERENCES:
patent: 2479942 (1949-08-01), Lecher et al.
Poisel et al., Chem. Ber., 108, pp. 2917-2922, (1975).
Schmidt et al., Angew. Chem. Int. Ed., (Engl.), 16, No. 11, pp. 777-778, (1977).
Rappoport, "The Chemistry of the Cyano Group," pp. 84 & 85, Interscience N.Y., 1970.

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