Hydrochloric Acid → HCID 23021238, compound

Temperature

-78 °C

To a solution of diisopropylamine (1.01 mL, 7.2 mmol) in tetrahydrofuran (8 mL) under cooling to −78° C. were added a solution of 1.5M n-butyl lithium/hexane solution (4.4 mL). After stirring the solution at −78° C. for 1 hour, a solution of dimethyl 1,1-cyclohexanediacetate (685 mg) in tetrahydrofuran (7 mL) was added thereto. The solution was stirred at −78° C. for 1 hour. Methyl chloroformate (0.93 mL) was then added to the solution, and it was stirred at −78° C. for 1 hour. Water and 3N hydrochloric acid were added to the solution, and it was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution. The solution was dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=85:15) to give the title compound (490 mg).

1. stirringThe solution was stirred at −78° C. for 1 hour
2. stirringwas stirred at −78° C. for 1 hour
3. extractionwas extracted with ethyl acetate
4. washThe organic layer was washed in turn with water and saturated aqueous sodium chloride solution
5. dry with materialThe solution was dried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=85:15)

ORD record

ord-f59b3db4618b40eaa7d3595e1cf4cd0a

Source dataset

uspto-grants-2008_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07375115B2