Methyl iodide → HCID 58109721, compound

Participants

Reaction Steps

To a solution of (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-((S)-1-(4-(hydroxymethyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 0.02 mmol) in THF (5 mL) was added NaH (1.4 mg) at 0° C. After stirring for 1 h at rt, the mixture was cooled to 0° C., and CH3I (90 mg 0.78 mmol) was added. The mixture was stirred overnight at rt. The reaction was quenched with H2O, and the layers were separated. The aqueous layer was extracted with CH2Cl2 for two times. The organic layer was combined, washed with brine, dried over Na2SO4 and concentrated to give the crude product, which was purified by preparative TLC to give (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-((S)-1-(4-(methoxymethyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (10 mg, 71%).

Provenance & Evidence