Potassium Carbonate → Tert-butyl 4-(prop-2-yn-1-yl)piperidine-1-carboxylate

A solution of tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate (0.596 g, 2.62 mmol) in methanol (10 mL) was added with potassium carbonate (0.724 g, 5.24 mmol), and the mixture was stirred at room temperature. The reaction mixture was added with dimethyl (1-diazo-2-oxopropyl)phosphonate (0.500 g, 2.62 mmol), and the mixture was stirred at room temperature for additional 4 hours. The reaction mixture was concentrated, and then added with water, and the mixture was extracted with methylene chloride. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-(prop-2-ynyl)piperidine-1-carboxylate (0.393 g, 67%).

1. stirringthe mixture was stirred at room temperature for additional 4 hours
2. concentrationThe reaction mixture was concentrated
3. additionadded with water
4. extractionthe mixture was extracted with methylene chloride
5. washThe organic layer was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was evaporated
8. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

ORD record

ord-4f31e064e85e438eacccb1bed0403111

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156827B2