Process for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile
AssigneeShell Oil Company
InventorWilly D. Kollmeyer
Life of this patent
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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.
Claims3
A method for preparing 3-azabicyclo(3.1.0)hexane-2-carbonitrile which consists of the steps:
- (a) treating 3-azabicyclo(3.1.0)hexane with a compound containing active chloride, and forming a solution of 3-chloro-3-azabicyclo(3.1.0)hexane;
- (b) treating said solution with an alcoholic solution of a strong inorganic base and filtering the resulting suspension to give a solution of 3-azabicyclo(3.1.0)hex-2-ene;
- (c) treating said solution with sodium bisulfite in the presence of water to form the bisulfite adduct,
- (d) treating the resulting mixture with an alkali metal cyanide to form 3-azabicyclo(3.1.0)hexane-2-carbonitrile, and
- (e) isolating said 3-azabicyclo(3.1.0)hexane-2-carbonitrile.
Dependencies are inferred from the claim text.