Pyridine → Carbonic acid 1-chloroethyl ester (1S,2S)-2-fluorocyclohexyl ester

To a mixture of 1-chloroethyl chloroformate (1.0 mL), pyridine (1.0 mL), and dichloromethane (30 mL), (1S,2S)-2-fluorocyclohexanol [CSA No. 292150-03-9] (900 mg) dissolved in dichloromethane (10 mL) was added at −78° C. After stirring the resulting mixture overnight at room temperature, dichloromethane (30 mL) was added to the mixture. The resulting mixture was sequentially washed with 0.5 N hydrochloric acid and saturated aqueous sodium chloride solution, and 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 (480 mg).

1. additionwas added at −78° C
2. washThe resulting mixture was sequentially washed with 0.5 N hydrochloric acid and saturated aqueous sodium chloride solution
3. dry with materialdried 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-8aca998ab7894999ad3148bfa6ff2ca9

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436009B2