Process for preparing 3-azabicyclo(3.1.0)hexane-2-carboxylic aci

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

1980-07-07

1981-07-21

Daus, Donald G.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603265B, C07D20952

Patent

active

042798213

ABSTRACT:
3-Azabicyclo(3.1.0)hexane-2-carboxylic acid, a plant gametocide, is prepared by effecting reaction between cis 2-aminomethylcyclopropyl-1,1-dimethyl acetal and a cyanide in the presence of a liquid lower-alkanecarboxylic acid; treating the resulting N-alkanoyl-3-azabicyclo(2.1.0)hexane-2-carbonitrile with a strong acid; treating the resulting 3-alkanoyl-3-azabicyclo(3.1.0)hexane-2-carboxylic acid with strong acid to form the desired 3-azabicyclo(3.1.0)hexane-2-carboxylic acid.

REFERENCES:
patent: 4047930 (1977-09-01), Kerr
patent: 4217283 (1980-08-01), Mason et al.
Noller, C., "Chemistry of Organic Compounds", W. B. Saunders Co., 1965, 3rd Edition, pp. 269, 275, 276.
B. Witkop et al., Chem. Abstracts 75:64234k (1971), Synthesis & X-ray Analysis of cis-3,4-methylene-L-proline.

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