Pyridine → HCID 86696314, compound

Temperature

-78 °C

To a solution of diacetone-D-glucose (1.56 g, 6 mmol) and pyridine (1.09 g, 1.12 mL, 13.8 mmol) in methylene chloride (6 mL) at −78° C. was added slowly a solution of 1-chloroethyl chloroformate (970 mg, 732 μl, 6.78 mmol) in methylene chloride (4 mL). After addition, the reaction mixture was allowed to stir at −78° C. for 1.5 h. Then the cold bath was removed and the reaction mixture was warmed up to room temperature. The reaction mixture was concentrated in vacuo and taken up in diethyl ether. The precipitate was filtered and the solid was washed thoroughly with diethyl ether. The filtrate and washing solutions were combined and concentrated to give 2.135 g of 1-chloroethyl (3aS,5S,6R,6aS)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-yl carbonate as clear light yellow thick oil, which was used directly without further purification.

1. additionAfter addition
2. customThen the cold bath was removed
3. temperaturethe reaction mixture was warmed up to room temperature
4. concentrationThe reaction mixture was concentrated in vacuo
5. filtrationThe precipitate was filtered
6. washthe solid was washed thoroughly with diethyl ether
7. washThe filtrate and washing solutions
8. concentrationconcentrated

ORD record

ord-5a516c154e434485a0014fdde881c3cc

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993614B2