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Synthesis 2000; 2000(5): 667-672
DOI: 10.1055/s-2000-6391
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A Practical Synthesis of para Di- and Mono-Substituted Benzhydrylamines from Benzhydrol Precursors

Mathieu Laurent* , Jacqueline Marchand-Brynaert
  • *Université catholique de Louvain, Laboratoire de Chimie Organique de Synthèse, Bâtiment Lavoisier, place Louis Pasteur 1, B-1348 Louvain-la-Neuve, Belgium; Fax + 32(10)47 41 68; E-mail: marchand@chor.ucl.ac.be
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Publication Date:
31 December 2000 (online)

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A series of para-substituted benzhydrylamines 6 were obtained by substitution of the corresponding benzhydrol precursors 1 with phenyl carbamate 2 under acidic conditions, followed by basic hydrolysis of the carbamate intermediates 3. One unsymmetrical intermediate 3i has been resolved by preparative chiral chromatography. Subsequent deprotection of the carbamate function led to the recovery of enantiomerically pure (+)- and (-)-4-chlorobenzhydryl amines.

benzhydrylamines - chiral chromatography - (+)-4-chlorobenzhydrylamine - (-)-4-chlorobenzhydrylamine - hydrolyses - deprotection

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