Use of Dibutyl[ 14 C]formamide as a Formylating Reagent in the Vilsmeier – Haack Reaction and Synthesis of a 14 C‐Labeled Novel Phosphodiesterase‐4 (PDE‐4) Inhibitor
2005; Wiley; Volume: 88; Issue: 5 Linguagem: Inglês
10.1002/hlca.200590075
ISSN1522-2675
AutoresJonathan Z. Ho, Charles S. Elmore, Michael A. Wallace, Dan Yao, Matthew P. Braun, Dennis Dean, David G. Melillo, Cheng‐yi Chen,
Tópico(s)Chemical synthesis and alkaloids
ResumoAbstract A simple, high‐yielding synthesis of dibutyl[ 14 C]formamide ([ 14 C]DBF; 1 ) from 14 CO 2 was developed ( Scheme 1 ): reaction of LiBEt 3 H and 14 CO 2 followed by aqueous workup gave H 14 CO 2 H in high yield. Conversion of the [ 14 C]formic acid to 1 was effected by a standard carbodiimide coupling procedure. The utility of 1 as an alternative to dimethyl[ 14 C]formamide ([ 14 C]DMF) in alkylation reactions and in the [ 14 C] Vilsmeier–Haack reaction was demonstrated for several substrates ( Table 2 ). A 14 C‐labeled phosphodiesterase‐4 (PDE‐4) inhibitor, [ 14 C]‐ 2 , was synthesized by application of this technology ( Scheme 2 ).
Referência(s)