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Synthesis 1992; 1992(1/2): 229-234
DOI: 10.1055/s-1992-34183
DOI: 10.1055/s-1992-34183
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.
A Diastereoselective Synthesis of (dl)-1,3-Diphenyl-1,3-propanediamines
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Publikationsverlauf
Publikationsdatum:
18. September 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/19920102/lookinside/thumbnails/10.1055-s-1992-34183-1.jpg)
A large-scale and practical synthesis of (dl)-1,3-diphenyl-1,3-propanediamine (1) has been achieved by a highly diastereoselective phenylcerium dichloride addition to 1-tert-butoxycarbonyl-4,5-dihydro-5-phenylpyrazole (3). Alkylcerium addition reaction to the corresponding 5-alkyl substituted 1-Boc-4,5-dihydropyrazoles was less satisfactory mainly giving ring-cleaved products. Further elaboration of the diamine 1 to the N-substituted derivatives 8a-f bearing N-methyl, N-ethyl, N-isopropyl, N-neopentyl, N-benzyl, and N-mesitylmethyl groups is described.