Ethyl 6-oxo-3-azabicyclo[3.2.1]octane-3-carboxylate ethylene ketal → Ethyl 6-oxo-3-azabicyclo(3.2.1)octane-3-carboxylate

HRID 597972Notes

Reaction equation

HRID 597972 reaction equation
[CH2:1]1O[C:4]([N:8]2[CH2:14][CH:13]3[CH2:15][CH:10]([CH2:11][C:12]3=[O:16])[CH2:9]2)([O:5]CC)[O:3][CH2:2]1>S(=O)(=O)(O)O>[O:16]=[C:12]1[CH2:11][CH:10]2[CH2:15][CH:13]1[CH2:14][N:8]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:9]2

Participants

3

Reactant 1

HCID 86602199Ethyl 6-oxo-3-azabicyclo[3.2.1]octane-3-carboxylate ethylene ketal

Product 1

HCID 53302214Ethyl 6-oxo-3-azabicyclo(3.2.1)octane-3-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A 2% solution of aqueous sulfuric acid (100 ml) was added to ethyl 6-oxo-3-azabicyclo[3.2.1]octane-3-carboxylate ethylene ketal (6.72 g, 27.9 mmol) and the mixture was allowed to stir for 1 h. The mixture was then extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over potassium carbonate, filtered, concentrated by rotary evaporation, and then distilled on a Kugelrohr apparatus (0.2 mm Hg, 132-162° C.) to yield a clear colorless oil (3.49 g, 64%).

Workup

  1. extractionThe mixture was then extracted with ethyl acetate (2×100 ml)
  2. dry with materialThe combined organic layers were dried over potassium carbonate
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. distillationdistilled on a Kugelrohr apparatus (0.2 mm Hg, 132-162° C.)

Sources & evidence

ORD record
ord-784900b0f1e246e4972414d37229b172
Source dataset
uspto-grants-2011_03
Patent number
US07897611B2

Reaction notes

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