Trimethylsilyl triflate → HCID 15117214, compound

Participants

Reaction Steps

To a solution of 4-acetyl-1-allyloxycarbonyl-1,2,3,6-tetrahydropyridine (1.33 g) and triethylamine (1.06 ml) in dichloromethane (50 ml) was added trimethylsilyl trifluoromethanesulfonate (2.2 ml) at 0° C. After stirring for 4 hours, a solution of (3R,4R)-4-acetoxy-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (1.82 g) and zinc bromide (1.86 g) in ethyl acetate (10 ml) was added to the mixture, and the resultant mixture was stirred for 1 hour at 0° C. The reaction mixture was taken up into a mixture of ethyl acetate (200 ml) and water (200 ml). After adjusting pH to 4 with aqueous sodium hydrogen carbonate, the organic layer was separated, washed with brine, dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (40 g) eluting with a mixture of n-hexane and ethyl acetate (9:1-3:7, V/V) to give (3S,4R)-4-[2-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-2-oxoethyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (1.80 g).

Provenance & Evidence