Ethanol → Ethyl 1-azabicyclo[2.2.1]heptane-7-carboxylate

HRID 2223195Notes

Reaction equation

HRID 2223195 reaction equation
Cl.[N:2]12[CH:8]([C:9]([OH:11])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.C([O-])(O)=O.[Na+].[Na+].[Cl-].[CH2:19](O)[CH3:20]>S(=O)(=O)(O)O>[N:2]12[CH:8]([C:9]([O:11][CH2:19][CH3:20])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

6

Reactant 4

HCID 702EthanolHCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 159465631-Azabicyclo[2.2.1]heptane-7-carboxylic acid--hydrogen chloride (1/1)

Product 1

HCID 22291193Ethyl 1-azabicyclo[2.2.1]heptane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 1-azabicyclo[2.2.1]heptane-7-carboxylic acid hydrochloride (1.20 g, 6.76 mmol) in absolute ethanol (10 mL) and concentrated sulfuric acid (2 mL) was refluxed for 8 h. The reaction mixture was cooled and then basified with saturated aqueous NaHCO3 to pH 8-9. The solution was saturated with solid NaCl and extracted with chloroform (4×20 mL). The combined chloroform extracts were dried over Na2SO4, filtered and concentrated by rotary evaporation to give a light brown liquid. This was purified by Kugelrohr distillation at 120° C. and 2.5 mm pressure to afford 1.00 g (90%) as a colorless liquid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with chloroform (4×20 mL)
  3. dry with materialThe combined chloroform extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customto give a light brown liquid
  7. distillationThis was purified by Kugelrohr distillation at 120° C.
  8. custom2.5 mm pressure to afford 1.00 g (90%) as a colorless liquid

Sources & evidence

ORD record
ord-791693e2b6314d1582548cc6f3c64132
Source dataset
uspto-grants-2008_05
Patent number
US07375110B2

Reaction notes

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