Twisted amide reduction under Wolff-Kishner conditions: synthesis of a benzo-1-aza-adamantane derivative |
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Authors: | Bashore Crystal G Samardjiev Ivan J Bordner Jon Coe Jotham W |
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Institution: | Pfizer Global Research and Development, Groton Laboratories, Pfizer Inc., Groton, CT 06340, USA. |
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Abstract: | A synthesis of 4,5-benzo-1-aza-tricyclo4.3.1.1(3,8)]undecane (1), a benzo-1-aza-adamantane derivative, is described and features a previously unknown application of the Wolff-Kishner reduction of a nonresonance stabilized or "twisted" amide. An intermediate amino ester is converted to a severely "twisted amide", which, when exposed to hydrazine in alcohol, provides the corresponding "twisted" amino hydrazone. Wolff-Kishner conditions (KOH/ethylene glycol, 200 degrees C) provide the reduced target 1 without hydrolysis to amino acid derivatives. These operations are conveniently performed in a single flask in high yield. |
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