Triphenylphosphine → (S)-(-)-methyl 3-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy)-5-((2-oxopyrrolidin-3-yl)oxy)benzoate

Participants

Reaction Steps

To a stirring mixture of Methyl 3-hydroxy-5-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]benzoate (7 g) (Intermediate 7) and (R)-(+)-3-hydroxy-2-pyrrolidinone (Intermediate 16) (2.4 g) in dry THF (200 mL) taken in round bottomed flask fitted with anhydrous CaCl2 guard tube, triphenyl phosphine (11.3 g) was added. Diisopropyl azodicarboxylate (DIAD) (6.2 mL) in dry THF (10 mL) was added drop wise to the above reaction mixture. The reaction was stirred at room temperature. Reaction was monitored by TLC for completion. After completion, reaction mixture was concentrated under vacuum to remove the solvents. Diluted with DCM and coated over silica gel and chromatographed to furnish the product as white solid (6 g).

Provenance & Evidence