Development of a Scaleable Synthesis of a Partial Nicotinic Acid Receptor Agonist

RD Wilson, E Cleator, MS Ashwood…

Index: Wilson, Robert D.; Cleator, Ed; Ashwood, Michael S.; Bio, Matthew M.; Brands, Karel M.J.; Davies, Antony J.; Dolling, Ulf-H; Emerson, Khateeta M.; Gibb, Andrew D.; Hands, David; McKeown, Arlene E.; Oliver, Steven F.; Reamer, Robert A.; Sheen, Faye J.; Stewart, Gavin W.; Zhou, George X. Organic Process Research and Development, 2009 , vol. 13, # 3 p. 543 - 547

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Citation Number: 4

Abstract

A practical and efficient synthesis of 1, 4, 5, 6-tetrahydro-3-(1 H-tetrazol-5-yl) cyclopenta [c] pyrazole, 1, is described. A new one-pot process has been developed, starting from the commercially available 1 H-tetrazole-5-carboxylic acid-ethyl ester sodium salt which is reacted in a pseudo-Claisen condensation reaction with cyclopentanone, followed by the addition of hydrazine.