(-)-Epichlorohydrin → (S)-2-(4-Bicyclo[3.3.1]non-9-yl-phenoxymethyl)-5-fluoromethyl-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-yl-amine (1.1 g, 3.5 mmol) (prepared from 4-bicyclo[3.3.1]non-9-yl-phenol and R-epichlorohydrin employing the procedures in Steps 1 through 2 of Example 1) in t-butanol (13 mL) was added 0.82 g (0.63 mmol) of 4-fluoro-but-2-ynoic acid ethyl ester (prepared in accordance with the procedures as described in Poulter, J Org Chem 1981, 46, 1532). The reaction mixture was refluxed for 6 hours after which it was concentrated and loaded on silica gel column and eluted with 1-6% EtOH/CH2Cl2 to afford 0.31g of the title compound. [α]D25 −26.00 (c 0.5, CHCl3).

Provenance & Evidence