Diethyl Ether → trans-2-Aminocyclohexanecarboxylic acid

HRID 127173Notes

Reaction equation

HRID 127173 reaction equation
[C@@H:1]1(C(O)=O)[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].C(Cl)(Cl)Cl.[N-:17]=[N+]=[N-].[Na+].CCOCC>S(=O)(=O)(O)O>[NH2:17][C@@H:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 33557Sodium AzideHCID 720895(1R,2R)-(-)-1,2-Cyclohexanedicarboxylic acid

Product 1

HCID 2724640trans-2-Aminocyclohexanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Trans-cyclohexane-1,2-dicarboxylic acid (8.105 g; racemic modification) is dissolved in conc. sulfuric acid (25 ml) and chloroform (50 ml) and kept at a temperature of 45° C., to which is added sodium azide (3.6 g) in one hour. After this, the solution is stirred for 90 minutes, added with ice water (25 ml) and is added with ether to remove chloroform. Barium carbonate (90 g) is added to the water layer of the solution to effect the neutralization. Barium sulfate is removed from the solution by filtration and the filtrate is concentrated to dryness to result in needle crystals of rac-trans-2-aminocyclohexanecarboxylic acid (referred to as A) having the following characteristics. When a corresponding rac-cis-compound is used as starting material, there is obtained the corresponding cis-compound i.e. rac-cis-aminocyclohexanecarboxylic acid, referred to as B).

Workup

  1. customkept at a temperature of 45° C., to which
  2. customto remove chloroform
  3. additionBarium carbonate (90 g) is added to the water layer of the solution
  4. customBarium sulfate is removed from the solution by filtration
  5. concentrationthe filtrate is concentrated to dryness

Sources & evidence

ORD record
ord-ce530529c0df4fd5b00b5bb28ffac51f
Source dataset
uspto-grants-1981_03
Patent number
US04255347

Reaction notes

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