HCID 67508601, compound → HCID 67517470, compound

Participants

Reaction Steps

To a solution of 4-[6-(1-tert-butoxycarbonylamino-cyclopropyl)-pyridin-3-yl]-benzoic acid methyl ester (0.68 g, 1.8 mmol) in THF (20 mL) was added Ti(Oi-Pr)4 (0.54 mL, 1.8 mmol). To this mixture was slowly added EtMgBr (3M in Et2O, 1.2 mL, 3.7 mmol) over 30 minutes. The reaction was allowed to stir at room temperature for 1 h. Ti(Oi-Pr)4 (1.1 mL, 3.2 mmol) and EtMgBr (3M in Et2O, 1.2 mL, 3.7 mmol) were again added to the solution and the reaction stirred for 30 minutes. The mixture was quenched with water and extracted with EtOAc (3×100 mL). The combined extracts were washed with water, brine and dried with MgSO4. The mixture was filtered, concentrated and the residue purified by reverse phase HPLC to give (1-{5-[4-(1-hydroxy-cyclopropyl)-phenyl]-pyridin-2-yl}-cyclopropyl)-carbamic acid tert-butyl ester (0.05 g, 1.4 mmol) as a brown solid, m/z 367.7 [M+H]+.

Provenance & Evidence