Hydrochloric Acid → HCID 21998677, compound

A solution of 5.0 g of cyclopropane-1,1-diacetonitrile in 200 ml of methanol was cooled to −15° C., and 4.95 g of cobalt chloride hexahydrate and 4.15 g of sodium borohydride were added thereto in this order, followed by stirring at that temperature for 15 minutes. The reaction mixture was made acidic by addition of 2N hydrochloric acid and then heated to room temperature, at which the mixture was stirred for 15 minutes, followed by concentration under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The aqueous layer was adjusted to pH 9 with a 5N sodium hydroxide aqueous solution, followed by filtration. Chloroform was added to the filtrate, and the organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 1.63 g of the title compound, which had the following physical properties.

1. stirringwas stirred for 15 minutes
2. concentrationfollowed by concentration under reduced pressure
3. additionWater was added to the residue
4. extractionthe mixture was extracted with ethyl acetate
5. filtrationfollowed by filtration
6. additionChloroform was added to the filtrate
7. washthe organic layer was washed with a saturated sodium chloride aqueous solution
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-1444b334a8224c16b85bb930b481e4c1

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06228866B1