Hydrochloric Acid → HCID 68643997, compound

HRID 2388703Notes

Reaction equation

HRID 2388703 reaction equation
Cl.C([N:5]1[CH2:10][CH2:9][C:8]2(N3CCCC3)[O:11][N:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:7]2[CH:6]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=O)C>>[C:24]1([CH:6]2[C:7]3[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:12][O:11][C:8]=3[CH2:9][CH2:10][NH:5]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 68643979HCID 68643979, compound

Product 1

HCID 68643997HCID 68643997, compoundYield 50%

Conditions

Temperature
130 °C

Procedure

Conc. HCl (12 ml) was added to ethyl 5-acetyl-4-phenyl-7a-(pyrrolidin-1-yl)-3a,4,5,6,7,7a-hexahydroisoxazolo[4,5-c]pyridine-3-carboxylate (2 g) at 0° C., and the reaction mixture was heated to 130° C. for 5 h. The hydrochloric acid was evaporated under reduced pressure and the residue was dissolved in dichloromethane and basified with sodium carbonate solution. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with brine solution and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give the crude compound which was used in the next step without further purification. Yield: 50%.

Workup

  1. customThe hydrochloric acid was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organic layers were washed with brine solution
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3bfc85d0a6ef4d5da6a9f878f7aee0a4
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

Loading…