Hexane → 3-((Tert-butoxy)carbonyl)-3-azabicyclo(3.1.0)hexane-6-carboxylic acid

HRID 340741Notes

Reaction equation

HRID 340741 reaction equation
C([O:3][C:4]([CH:6]1[CH:11]2[CH:7]1[CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10]2)=[O:5])C.[OH-].[Na+].CCCCCC.C(OCC)(=O)C>C(O)C>[C:15]([O:14][C:12]([N:9]1[CH2:8][CH:7]2[CH:11]([CH:6]2[C:4]([OH:5])=[O:3])[CH2:10]1)=[O:13])([CH3:18])([CH3:16])[CH3:17]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 235533633-Tert-butyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

Product 1

HCID 533952883-((Tert-butoxy)carbonyl)-3-azabicyclo(3.1.0)hexane-6-carboxylic acidYield 96.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The tert-butyl 6-ethoxycarbonyl-3-azabicyclo[3.1.0]hexane-3-carboxylate exo-isomer (613 mg, 2.40 mmol) prepared in Example 2 was dissolved in 6 mL of ethanol and 2N NaOH (2.40 mL, 4.80 mmol) was added dropwsie at 0° C. After stirring at room temperature for 3 hours, the completion of the reaction was confirmed by TLC (hexane:ethyl acetate=6:1). After the reaction was completed, the reaction mixture was concentrated under reduced pressure and then extracted by adding methylene chloride and water. After removing the organic layer containing byproducts, the aqueous layer was acidified with 1N HCl and extracted with methylene chloride. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain 527 mg (96.5%) of the target compound.

Workup

  1. customprepared in Example 2
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. extractionextracted
  4. additionby adding methylene chloride and water
  5. customAfter removing the organic layer
  6. additioncontaining byproducts
  7. extractionextracted with methylene chloride
  8. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4967a9f8dac04b709ad56c346a8abbb2
Source dataset
uspto-grants-2014_11
Patent number
US08895602B1

Reaction notes

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