Triethylamine → Benzyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate

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Reaction Steps

To a solution of tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-8-azabicyclo[3.2.1]oct-2-ene-8-carboxylate (Intermediate G21.2, 1.93 g, 5.76 mmol) in dry Dioxane (20 ml), 4 M hydrogen chloride 1,4 dioxane (5.76 ml, 23.03 mmol) was added and the solution was stirred for 1 h. Then, solvent was removed. Crude was dissolved in dry DCM (20.00 ml), N-(benzyloxycarbonyloxy)succinimide (1.964 ml, 6.91 mmol) and triethylamine (3.14 ml, 23.03 mmol) were added and the suspension was stirred for 1 h. Then, solvent was removed and the product was purified by Biotage Si 25 g with a gradient of heptane and EtOAc affording the title compound (810 mg, 2.194 mmol, 38.1% yield) as a white solid.

Provenance & Evidence