tert-Butanol → 3-Azabicyclo[3.1.0]hexane-2-carboxylic acid

HRID 443976Notes

Reaction equation

HRID 443976 reaction equation
Cl[CH:2]1[CH:8]2[CH:6]([CH2:7]2)[CH2:5][NH:4][C:3]1=[O:9].C([OH:14])(C)(C)C>>[CH:8]12[CH2:7][CH:6]1[CH2:5][NH:4][CH:2]2[C:3]([OH:9])=[O:14]

Participants

3

Reactant 2

HCID 6386tert-ButanolHCID 541009355-Chloro-3-azabicyclo(4.1.0)heptan-4-one

Product 1

HCID 37794533-Azabicyclo[3.1.0]hexane-2-carboxylic acid

Procedure

0.9 g of IV prepared in experiment (c) was refluxed for 16 hours in t-butanol containing 0.5 g potassium. The reaction mixture was allowed to cool, the solvent was evaporated under reduced pressure and the residue was poured into 20 ml of water. Dilute (4 N) hydrochloric acid was added until the solution was acidic and then extracted thrice with methylene chloride. The water layer was then passed over a column filled with Dowex 50W-X8 ion-exchange resin. Eluting the resin with ammonium hydroxide then gave the cis isomer of 3-azabicyclo(3.1.0)hexane-2-carboxylic acid.

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated under reduced pressure
  3. additionthe residue was poured into 20 ml of water
  4. additionDilute (4 N) hydrochloric acid
  5. additionwas added until the solution
  6. extractionextracted thrice with methylene chloride
  7. additionfilled with Dowex 50W-X8 ion-exchange resin
  8. washEluting the resin with ammonium hydroxide

Sources & evidence

ORD record
ord-181a11111af44f3bbe5d338143efef92
Source dataset
uspto-grants-1981_04
Patent number
US04262124

Reaction notes

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