Acetic Acid → HCID 54463660, compound

HRID 256900Notes

Reaction equation

HRID 256900 reaction equation
[N:1]12[CH2:9][CH:5]([C:6](=O)[CH2:7]1)[CH2:4][CH2:3][CH2:2]2.C(O)(=O)C.C([O-])(=O)C.[NH4+].[C:19]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])#[N:20]>C1(C)C=CC=CC=1.O>[N:1]12[CH2:9][CH:5]([C:6](=[C:21]([C:19]#[N:20])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:7]1)[CH2:4][CH2:3][CH2:2]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 4183471-azabicyclo[3.2.1]octan-6-oneHCID 517165Ammonium Acetate

Product 1

HCID 54463660HCID 54463660, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 1-azabicyclo[3.2.1]octan-6-one (41.25 g, 0.33 mol), acetic acid (2 ml), ammonium acetate (1.25 g) and ethyl cyanoacetate (37 g, 0.33 mol) in toluene (500 ml) was refluxed with a Dean-Stark water separator for 40 h. The toluene phase was extracted with 3×200 ml 5M HCl solution. The water phase was basified with 28% ammonium hydroxide solution and extracted with ether (4×200 ml). The organic phases were dried over magnesium sulfate and evaporated. The residue was purified by column chromatography (eluent CH2Cl2 /MeOH (9:1), yield 41 g of the title compound.

Workup

  1. extractionThe toluene phase was extracted with 3×200 ml 5M HCl solution
  2. extractionextracted with ether (4×200 ml)
  3. dry with materialThe organic phases were dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by column chromatography (eluent CH2Cl2 /MeOH (9:1), yield 41 g of the title compound

Sources & evidence

ORD record
ord-69fbf026b2a4453a87f49388ef1fdc77
Source dataset
uspto-grants-1993_11
Patent number
US05260314

Reaction notes

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