89772-93-0Relevant academic research and scientific papers
Preparation of (R)-(+)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide: synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine
Castro, Alejandro,Ramirez, Johana,Juarez, Jorge,Teran, Joel L.,Orea, Laura,Galindo, Alberto,Gnecco, Dino
, p. 2699 - 2708 (2008/09/19)
We describe the transformation of (R)-(-)-1-(2'-hydroxy-1'-phenylethyl)piperidin-2-one 1 into (R)-(-)-3-phenyl-2,3,5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium bromide 2 using POBr3. Reduction of 2 with Red-Al at -78 °C gave (3R,8aR)-(-)-3-phenylhexahydro-2H-oxazolo[3,8-a]-pyridine 3 as a single diastereoisomer. The synthetic potential of these transformation is illustrated by the enantiopure synthesis of (S)-(+)-coniine, (R)-(-)-coniceine and (R)-(+)-anabasine.
