Ethyl pent-2-yn-1-oate → (S)-2-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

Participants

Reaction Steps

To a solution of (S)-5-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.26 g, 0.828 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-bicyclo[3.3.1]non-9-yl phenol (prepared with the same procedure as set forth in steps 1 and 2 of Example 20), in ethanol (5 mL) was added ethyl 2-pentynoate (0.157 g, 1.24 mmol). The reaction mixture was heated at reflux for 14 hrs and then cooled to room temperature. The reaction mixture was concentrated and loaded onto a silica gel column, and eluted with 4-6% methanol/methylene chloride to afford 120 mg of (S)-2-(4-bicyclo[3.3.1]non-9-yl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one. [α]D25 −36.89 (c 0.501, CHCl3).

Provenance & Evidence