Water → N-[2-({(2S)-3-[4-(5-Fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-hydroxyphenyl]acetamide

Participants

Reaction Conditions

Reaction Steps

N-[2-({(2S)-3-[4-(5-Fluoro-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)-1-piperidinyl]-2-hydroxypropyl}oxy)-4-methoxyphenyl]acetamide, obtained in Example 32iii), (300 mg, 0.6 mmol) was dissolved in dichloromethane (5 ml) and stirred under nitrogen (N2) at ambient (20-22° C.) temperature. Boron tribromide solution (1 M in dichloromethane, 2 ml, 2 mmol) was added dropwise. After stirring at ambient temperature for 17 hr dichloromethane (5 ml) and water (5 ml) were added. After 1 hr the solvent was removed in vacuo. The residue was purified by gradient flash chromatography on silica gel (CH2Cl2/MeOH, 100/0 to 70/30) and lyophilized yielding the title compound as a white solid (134 mg, 49%).

Provenance & Evidence