Carbon Dioxide → 5-({[(2R)-1-Methyl-2-pyrrolidinyl]methyl}oxy)-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

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Reaction Steps

2-[(Phenylmethyl)oxy]-N-3-pyridinyl-5-{[(2R)-2-pyrrolidinylmethyl]oxy}benzamide (may be prepared as described in Example 44; 250 mg, 0.62 mmol) was added to formic acid (4.5 ml) at 5° C., followed by 40% aqueous formaldehyde (2.4 ml). When the initial evolution of carbon dioxide had subsided, the mixture was refluxed for 2 h. After the solution was cooled, the pH of the solution was adjusted to 7-8 by adding aqueous NaHCO3 solution. The mixture was extracted with dichloromethane. The organic layer was dried over Na2SO4, and concentrated to obtain a crude product, which was purified by prep-HPLC to yield the title compound as a white solid. 47 mg.

Provenance & Evidence