Hydrochloric Acid → 1-Benzyloxymethyl-1H-pyrazole-3-boronic Acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-benzyloxymethyl-1H-pyrazole (200 mg, 1.06 mmol) in THF (5 mL) at 0° C. is added n-BuLi (0.51 mL of 2.5M in THF, 1.28 mmol) and the mixture is stirred at 0° C. for 30 min. To this is added trimethyl borate (551 mg, 5.3 mmol) dropwise then the mixture is allowed to warm to RT overnight. The light yellow solution is acidified with 1N HCl (12.8 mL) and the THF is removed under reduced pressure. The aqueous phase is purified by reverse phase MPLC using a gradient of 0-60% MeCN/water as eluent. The solvent is concentrated until a precipitate forms. The mixture is cooled to 0° C. and the solid filtered to give the title compound.

Provenance & Evidence