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

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.

1. filtrationthe mixture was filtered through Celite
2. concentrationThe filtrate was concentrated
3. dissolutionThe resulting residue was dissolved in acetonitrile (15 mL)
4. temperaturechilled
5. stirringstirred
6. stirringThe reaction mixture was then stirred at room temperature for 4 hours
7. concentrationSubsequently, the mixture was concentrated
8. additionethyl acetate was added
9. washThe mixture was sequentially washed with a 5% aqueous citric acid solution
10. dry with materialby drying over magnesium sulfate
11. customEvaporation of the solvent

ORD record

ord-b4c486e680a4457390d1bef209f5866f

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902367B2