Preparation of dl-proline and dl-ornithine from 1,1,1,5-tetrachloropentane

Summary

• 1. DL-Prollne was prepared by several routes from 1, 1, 1, 5-tetracltloropentane. It was shown that the best of these routes to the preparation of DL-proline is the following:

  

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• 2. DL-Qrsdthine was prepared from 1, 1, 5-trichloro-l-pentene in the following way:

  $$\begin{gathered} Cl(CH_2 )_3 CH = CCl_2 \to C_6 H_4 (CO)_2 N(CH_2 )_3 CH = CCl_2 \to \hfill \\ \to C_6 H_4 (CO)_2 N(CH_2 )_3 CHCl - CO_2 H \to NH_2 (CH_2 )_3 CHNH_2 CO_2 H \hfill \\ \end{gathered} $$

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• 3. it was shown that, under the action of ammonia or the potassium derivative of phthalimide, 1, 1, 1, 2, 5-pentachloropentane is converted into 4, 5, 5-trichloro- -pentenylamine or N-(4, 5, 5-trichloro4-pentenyl) phthalimide, respectively. No replacement of the chlorine atom in the α-position to the CCI₃ group occurs.