Process development of the synthetic route to R116301

M Guillaume, J Cuypers…

Index: Guillaume, Michel; Cuypers, Jef; Dingenen, Jul Organic Process Research and Development, 2007 , vol. 11, # 6 p. 1079 - 1086

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Citation Number: 10

Abstract

We describe in this paper the synthesis of compound 1 (R116301), which was developed to prepare pilot scale quantities (20–50 kg) of drug substance. The synthesis involves the s BuLi deprotonation of Boc-protected piperidone acetal 2, followed by benzaldehyde addition and ring closure to cyclic carbamate 4. Piperidine acetal 5 is resolved with Brown's acid and acylated. The ketone obtained after piperidine acetal deprotection undergoes reductive ...