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Synthesis 1994; 1994(5): 505-508
DOI: 10.1055/s-1994-25513
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Carbamate Oxime Reduction: A New Route to C3-Amino-1,4-benzodiazepines

Sylvie Bourrain* , Graham A. Showell
  • *Merck, Sharp and Dohme Research Laboratories, Neuroscience Research Centre, Terlings Park, Eastwick Road, Harlow, Essex CM20 2QR, England
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Publication Date:
17 September 2002 (online)

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A mild reduction method of C3-oximido-1,4-benzodiazepines to afford the C3-amino derivatives is described. The key step involves the formation of a carbamate oxime intermediate. The greater reactivity of the C3-(ethylaminocarbonyl)oximido-1,4-benzodiazepine towards hydrogenation, compared to the parent C3-oxime, enables the reduction to take place at ambient temperature using palladium-on-carbon. The mild conditions are more suitable for sensitive amines such as 3,5-diamino-1,4-benzodiazepines.