Hydrochloric Acid → HCID 77340548, compound

(+) 1-Azabicyclo[3.2.1]octan-6-one (-) camphorsulfonate (61.8 g, 135.0 mmol) and triethylamine (20.4 g, 202 mmol) and ethyl cyanoacetate (61.8 g, 547 mmol) were mixed and stirred at room temperature for 6 days. Toluene (120 ml) and water (120 ml) were added to the reaction mixture and the pH was adjusted to 2 with concentrated hydrochloric acid. The phases were separated and the water phase extracted with toluene (30 ml). The combined organic phases were washed with water (20 ml). The combined water phases were adjusted to pH=9.4 with NH3 (25% in water) and extracted with toluene (1×120 ml, 1×60 ml). The combined toluene extracts were evaporated. The residue was dissolved in ethanol (120 ml) and concentrated hydrochloric acid (16 ml) was added. The title compound precipitated in 22 g yield. Upon evaporation of the mother liquor and crystallization from ethanol (40 ml) further 14.6 g of the title compound was isolated.

1. customThe phases were separated
2. extractionthe water phase extracted with toluene (30 ml)
3. washThe combined organic phases were washed with water (20 ml)
4. extractionextracted with toluene (1×120 ml, 1×60 ml)
5. customThe combined toluene extracts were evaporated
6. dissolutionThe residue was dissolved in ethanol (120 ml)
7. additionconcentrated hydrochloric acid (16 ml) was added
8. customThe title compound precipitated in 22 g
9. customyield
10. customUpon evaporation of the mother liquor and crystallization from ethanol (40 ml) further 14.6 g of the title compound
11. customwas isolated

ORD record

ord-a4e6255a33ce4905902c71fd75224802

Source dataset

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05527813