Synthesis of (S)-3-heteroaryl-2-hydroxy-l-propyl benzoates by ‘ring switching’ methodology

(S)-5-Benzoyloxymethyl-3-[(E)-(dimethylamino)methylidene]tetrahydrofuran-2-one (6), prepared in 5 steps from L-glutamic acid (1), was used as precursor in a one step ‘ring switching’ synthesis of (S)-2-hydroxy-3-heteroaryl-l-propyl benzoates 13-18, 23, 24. In the reaction of 6 with 2-aminopyridine (21) and 2-amino-4,6-dimethylpyrimidine (22) the corresponding dimethylamine substitution products (25, 26) were obtained.