Method for producing an optically active 2,2-dimethylcyclopropanecarboxylic acid

• US 4,542,235 A
• Filed: 04/05/1983
• Issued: 09/17/1985
• Est. Priority Date: 04/12/1982
• Status: Expired due to Term

• Current Assignee: Sumitomo Chemical Company Limited
• Original Assignee: Sumitomo Chemical Company Limited
• Inventors: Katsura, Tadashi, Minai, Masayoshi, Suzukamo, Gohfu, Hamada, Kazuhiko
• Primary Examiner(s): Trousof, Natalie
• Assistant Examiner(s): Clarke, Vera C.
• Application Number:
  US06/482,259
• Time in Patent Office: 896 Days
• Field of Search: 562/401, 562/506
• US Class Current: 562/401
• CPC Class Codes: C07C 51/487 by treatment giving rise to chemical modification by chemisorption C07C51/47
• CPC Class Codes: C07C 61/04 Saturated compounds having a carboxyl group bound to a three or four-membered ring

Abstract

A method for producing an optically active 2,2-dimethylcyclopropanecarboxylic acid useful as an intermediate for dehydropeptidase I inhibitors, medicines and agricultural chemicals, which comprises reacting an optically active diphenylethylamine represented by the formula, ##STR1## wherein R₁ and R₂ are each a hydrogen atom or a lower alkyl group, with 2,2-dimethylcyclopropanecarboxylic acid in a solvent to achieve the optical purification of said acid.

Claims

1. A method for producing an optically active 2,2-dimethylcyclopropanecarboxylic acid which comprises reacting an optically active diphenylethylamine represented by the formula (I), ##STR3## wherein R₁ and R₂ are each a hydrogen atom or a lower alkyl group, with 2,2-dimethylcyclopropanecarboxylic acid in a solvent to achieve the optical purification of said acid.

2. A method as described in claim 1, wherein said 2,2-dimethylcyclopropanecarboxylic acid is a one containing the d-form in excess, and said optically active 2,2-dimethylcyclopropanecarboxylic acid is d-2,2-dimethylcyclopropanecarboxylic acid.

3. A method as described in claim 1, wherein said 2,2-dimethylcyclopropanecarboxylic acid is a one containing the l-form in excess, and said optically active 2,2-dimethylcyclopropanecarboxylic acid is l-2,2-dimethylcyclopropanecarboxylic acid.

4. A method as described in claim 2, wherein the optical excess rate of said 2,2-dimethylcyclopropanecarboxylic acid is not less than 30%.

5. A method as described in claim 1, wherein said optically active diphenylethylamine is either of d- or l-α

-phenyl-β

-(p-tolyl)ethylamine, d- or l-α

-(p-tolyl)-β

-phenylethylamine or d- or l-α

-phenyl-β

-phenylethylamine.

6. A method as described in claim 1, wherein the amount of the optically active diphenylethylamine used is 0.3 to 1.2 times by mole based on 2,2-dimethylcyclopropanecarboxylic acid, a starting material.

7. A method as described in claim 3, wherein the optical excess rate of said 2,2-dimethylcyclopropanecarboxylic acid is not less than 30%.