Pyridine → HCID 86677398, compound

1-Chloropropyl chloroformate [CAS No. 92600-20-9] (2.99 g) and pyridine (1.62 mL) were dissolved in dichloromethane (30 mL), and a solution of trans-2-fluorocyclohexanol [CAS No. 14365-32-3] (2.36 g) in dichloromethane was added dropwise thereto under ice-cooling. After stirring the resulting mixture overnight at room temperature, the reaction mixture was diluted with ethyl acetate, and sequentially washed with 1 N hydrochloric acid, water, and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate. The resulting mixture was filtered, and the filtrate obtained was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate) to obtain the captioned compound (2.731 g).

1. temperatureunder ice-cooling
2. washsequentially washed with 1 N hydrochloric acid, water, and saturated aqueous sodium chloride solution
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. filtrationThe resulting mixture was filtered
5. customthe filtrate obtained
6. concentrationwas concentrated under reduced pressure
7. customThe residue obtained
8. customwas purified by silica gel column chromatography (mixed solvent of heptane-ethyl acetate)

ORD record

ord-949fd56910474f16b94bdf8185c376c0

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436009B2