Norbornadiene → (5R)-3-(4-Iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

(5R)-5-(Azidomethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one (10.0 g, 29.1 mmol) was dissolved in 1,4-dioxane (100 ml). Bicyclo[2.2.1]hepta-2,5-diene (9.4 ml, 87.2 mmol) was added and the mixture heated to 100° C. for 24 h. The solution was cooled and purified by silica flash chromatography with 1-10% methanol in dichloromethane as eluent giving 7.2 g of the desired product.

Provenance & Evidence