Water → Tert-butyl 3-(hydroxymethyl)azepane-1-carboxylate

Participants

Reaction Steps

1-Benzyl perhydroazepin-3-yl methanol (1.30 g, 5.93 mmol) was dissolved in a 4.4% formic acid/methanol solution (30 mL). To this solution, 10% palladium on activated carbon (1.30 g) was added and the mixture was stirred at room temperature for 2 hours. Subsequently, water was added and the mixture was filtered through Celite. The filtrate was concentrated. The resulting residue was dissolved in acetonitrile (15 mL). While the solution was ice-chilled and stirred, triethylamine (1.81 mL, 13.0 mmol) and t-butyl dicarbonate (1.42 g, 6.52 mmol) were added. The reaction mixture was then stirred at room temperature for 4 hours. Subsequently, the mixture was concentrated and ethyl acetate was added. The mixture was sequentially washed with a 5% aqueous citric acid solution, a saturated aqueous sodium bicarbonate solution and brine, followed by drying over magnesium sulfate. Evaporation of the solvent gave 1.13 g (83%) of the desired compound as a colorless oil.

Provenance & Evidence