Diethyl Ether → (S)-N-methyl-N-methoxy 2(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a suspension of the hydroxy ester of Step 3 (4.519 g, 9.5 mmol) and N,O-dimethylhydroxylamine hydrochloride (2.777 g, 28.5 mmol) in 95 mL of anhydrous THF at 0° C. was added dropwise 3M EtMgBr in Et2O (22 mL 66 mmol) over ≃40 min. The mixture was then stirred at 0° C. for 30 min. and poured into ice-cold saturated NH4Cl. The product was extracted in EtOAc, dried over Na2SO4, and concentrated to yield the title compound.

Provenance & Evidence