Hydrochloric Acid → HCID 69456015, compound

Participants

Reaction Steps

To a solution of (2R)-N-((1R)-2-(7-(benzyloxy)-1H-indol-3-yl)-1-methylethyl)-2-hydroxy-2-pyridin-3-ylacetamide (283 mg, 0.681 mmol) in tetrahydrofuran (15 mL) is added a 2M solution of boranedimethyl sulfide complex in tetrahydrofuran (2.04 mL, 4.09 mmol), and the mixture is refluxed for 3 hours. To the reaction solution is added a 10% hydrogen chloride solution in methanol (30 mL), and the mixture is stirred for 30 minutes. The solvent is evaporated, and the residue is separated into a saturated aqueous sodium hydrogen carbonate solution and chloroform. The organic layer is washed with a saturated brine, and dried over sodium sulfate. The solvent is distilled off, and the obtained crude product is purified by silica gel column chromatography (a saturated ammonia solution in chloroform-methanol=100:1) to give the title compound (184.8 mg, yield: 68%).

Provenance & Evidence