Benzyl chloroformate → Benzyl 3-(hydroxymethyl)piperidine-1-carboxylate

3-Piperidinemethanol (3.59 g, 31.2 mmol) in 1,4-dioxane (8 mL) was mixed with potassium carbonate (4.55 g, 33.0 mmol), 1 M aqueous sodium hydroxide (2 mL) and benzyl chloroformate (5.20 mL, 36.4 mmol) under cooling with ice and stirred at room temperature for one day. After addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous potassium hydrogen sulfate and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v)) to give the title compound as a colorless oil (6.41 g, yield 83%).

1. temperatureunder cooling with ice
2. extractionthe reaction mixture was extracted with ethyl acetate
3. washthe organic layer was washed with saturated aqueous potassium hydrogen sulfate and saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1 (v/v))

ORD record

ord-d1f740b4296b456999041bb0c8205cf1

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216999B2