Acetic Acid → HCID 15117353, compound

Participants

Reaction Steps

To a solution of allyl (5R,6S)-3-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-t-butyldimethylsilyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.94 g) in tetrahydrofuran (38 ml) were added dropwise acetic acid (1.65 ml) and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1M, 9.6 ml) at 0° C. After standing at ambient temperature for 8 hours, the reaction mixture was taken up into a mixture of ethyl acetate (300 ml) and water (300 ml). After adjusting pH to around 7 with aqueous sodium hydrogen carbonate the organic layer was separated washed in turn with water and brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was chromatographed on silica gel (25 g) eluting with a mixture of n-hexane and ethyl acetate (9:1-3:7, V/V) to give allyl (5R,6S)-3-(1-allyloxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (281 mg).

Provenance & Evidence