Amino Acids and Peptides. XXVII. A Novel Reductive Cleavage of N-C-N Bonds with Sodium Borohydride

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概要

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• (3S)-tert-Butyl 2-benzyloxycarbonyl-1,2,3,4-tetrahydro-β-carboline-3-carbamate (III), prepared by the modified Curtius reaction of (3S)-2-benzyloxycarbonyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (II) with diphenyl phosphorazidate (DPPA) and triethylamine in tert-butyl alcohol, afforded 2-ethyloxycarbonylaminomethyl-3-(2-tert-butyloxy-carbonylamino) ethylindole (Va) by sodium borohydride reduction in ethanol, while reduction in 2-propanol gave the corresponding 2-propyl derivative (Vb) and the compound (VI) containing a novel diazocinoindole skeleton. The mechanism of the reductive cleavage was discussed. Tetrahydropyrrole analog (X) of III and 2-acetyl analog of III afforded the similar ring-cleavage products (XI and XV) by sodium borohydride reduction.

• 公益社団法人日本薬学会の論文
• 1977-07-25

著者

• 山田 俊一

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 塩入 孝之

  Faculty of Pharmaceutical Sciences, Nagoya City University

• 山田 俊一

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 塩入 孝之

  Faculty Of Pharmaceutical Sciences Nagoya City University

• 村戸 和夫

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 村戸 和夫

  Faculty Of Pharmaceutical Sciences University Of Tokyo

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