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

Participants

Reaction Steps

To a solution of (2S,6R)-2-(4-cyclohexyl-phenoxymethyl)-6-ethyl-2,3,5,6-tetrahydro-oxazolo[3,2-a]pyrimidin-7-one (108 mg, 0.41 mmol) in toluene (2 ml) was added manganese(IV) oxide (360 mg, 4.1 mmol). The reaction mixture was heated at reflux for three days. The reaction mixture was filtered without cooling and the filtrate concentrated and loaded on a silica gel column. The column was eluted with 2-7% isopropanol/methylene chloride to afford 8 mg of (S)-2-(4-cyclohexyl-phenoxymethyl)-6-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one. [α]D25 −22.40 (c 0.5, CHCl3).

Provenance & Evidence