Ammonium Chloride → [4-(2-Cyclopropyl-2-hydroxy-2-phenyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

(4-Methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (200 mg, 0.96 mmol) is dissolved in dry THF (10 mL) and it is cooled down to −78° C. After 1.6 M n-BuLi (3.0 mL, 4.8 mmol) is added at −78° C., the cooling bath is removed and the mixture is stirred at room temperature for 15 min. Then the reaction mixture is cooled down to −78° C. again and cyclopropyl-phenyl-methanone (0.68 mL, 4.8 mmol) is added. After the mixture is stirred for 30 min at −78° C., saturated NH4Cl aqueous solution (35 mL) is added and the reaction is warmed up to room temperature. EtOAc (70 mL) is added along with water (70 mL). The mixture is stirred for another 10 min and the aqueous layer is separated, extracted with EtOAc (2×35 ml). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 280 mg of the desired product.

Provenance & Evidence