88056-96-6

Upstream product

• 927-77-5 n-propylmagnesium bromide 
• 155796-94-4 (αR)-N-(2-hydroxy-1-phenylethyl)piperidine-2-one 
• 2234-82-4 1-propylmagnesium chloride 
• 154472-03-4 (3R,8aR)-(-)-3-phenyl-2,3,5,6,7,8-hexahydro-2H-oxazolo[3,8-a]pyridine 
• 344797-51-9 (1'R)-(-)-1-(2'-hydroxy-1'-phenyl-ethyl)-3,4-dihydro-(1H)-pyridin-2-one 
• 211919-57-2 (1'R)-(-)-1-(2'-hydroxy-1'-phenyl-ethyl)-(1H)-pyridin-2-one 
• 152555-02-7 (3R,8aR)-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 
• 683771-95-1 (1'R,6S)-(-)-1-(2'-hydroxy-1'-phenyl-ethyl)-6-n-propyl-piperidine-2-thione 
• 156873-53-9 (1'R,6S)-(+)-1-(2'-hydroxy-1'-phenyl-ethyl)-6-propyl-piperidin-2-one 
• 88056-92-2 (-)-2-cyano-6-phenyloxazolopiperidine 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 458-88-8 coniine 
• 555-92-0 (S)-coniine hydrochloride 

Relevant 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

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.

Syntheses of pyridin-4-ylium chirons: Applications in a synthesis of (+)-coniine

The compounds (3R,5S)-(+)-5-methyl-3-phenyl-2,3,5,6,7,8-hexahydro- oxazolo[3,2-a]pyridin-4-ylium iodide 4 and (3R,5S)-(+)-5-n-propyl-3-phenyl-2,3, 5,6,7,8-hexahydro-oxazolo[3,2-a]pyridin-4-ylium iodide 5 were synthesized in two steps starting from the bicyclic thiolactam trans (3R,2aS)-(-)-5-thio-3- phenyl-2,3,6,7,8,2a-hexahydro-oxazolo[3,2-a]pyridine 1. In addition, starting from 5 an enantiospecific synthesis of (+)-coniine 7 was achieved.

New methodology for the synthesis of enantiopure (3R,2aR)-(-)-3-phenyl-hexahydro-oxazolo[3,2-a]-pyridin-5-one: A synthesis of (S)-(+)-coniine

A new and efficient methodology for the enantiopure synthesis of (3R,2aR)-(-)-3-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one 3 starting from (1′R)-(-)-1-(2′-hydroxy-1′-phenyl-ethyl)-(1H)-pyridin-2-one 1 is described. In addition, the enantiospecific synthesis of (S)-(+)-coniine hydrochloride 6 in good yield from 3 is reported.

Asymmetric synthesis. XL. 2,3-Disubstituted piperidines via chiral non-racemic lactams

Optically pure 2,3-cis-disubstituted piperidines 7a and 7b have been prepared from chiral lactams 2. The first step involves C-2 functionalization with Grignard reagent, then a diastereoselective reduction of resulting oxazolidines 5 furnishes the desired