1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Benzyl-5-bromo-2-[(3r,4r)-3,4-dihydroxypyrrolidine-1-yl]pyridine

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Reaction Steps

A mixture of 4.0 g of 4-benzyl-5-bromo-2-pyridyl trifluoromethanesulfonate, 1.8 g of (3R,4R)-3,4-dihydroxypyrrolidine acetate, 3 ml of 1,8-diazabicyclo[5.4.0]-7-undecene and 5 ml of tetrahydrofuran was heated under stirring for 3 hours in an oil bath kept at 70° C. in a nitrogen atmosphere. After cooling as it was, the reaction mixture was extracted with ethyl acetate-water. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography and eluted with 10% methanol/ethyl acetate, to give 1.67 g of the target compound.

Provenance & Evidence