Hydroquinone → (2S,6S)-2-(4-cyclohexyl-phenoxymethyl)-6-methyl-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.85 g, 3.09 mmol), prepared in accordance with the procedures as set forth in Steps 1 and 2 of Example 1 and starting from R-epichlorohydrin and 4-cyclohexylphenol, and methyl methacrylate (3.72 g, 37.15 mmol) stabilized with hydroquinone was heated at 90° C. for 14 hrs. The reaction mixture was concentrated and loaded onto a silica gel column, eluted with 2-6% isopropanol/methylene chloride to afford (2S,6R)-2-(4-cyclohexyl-phenoxymethyl)-6-methyl-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one and (2S,6S)-2-(4-cyclohexyl-phenoxymethyl)-6-methyl-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one (total 0.79 g).

Provenance & Evidence