Quinine → HCID 54462553, compound

HRID 1199265Notes

Reaction equation

HRID 1199265 reaction equation
[CH:1]1([CH2:7][CH:8]=[CH:9][CH2:10][CH:11]([CH:15]([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COC1C=CC2N=CC=C([C@@H](O)[C@H]3N4C[C@H](C=C)[C@@H](CC4)C3)C=2C=1>CO>[CH:1]1([CH2:7][CH:8]=[CH:9][CH2:10][C@H:11]([CH:15]([CH3:17])[CH3:16])[C:12]([OH:14])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 3034034QuinineHCID 54462554HCID 54462554, compound

Product 1

HCID 54462553HCID 54462553, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

154.65 g (0.65 mol) of racemic 6-cyclohexyl-2-isopropyl-4-hexenoic acid and 210.5 g (0.65 mol) of anhydrous quinine are dissolved in 1 liter of methanol. The mixture is concentrated by evaporation and the residue is recrystallised from ether hexane. The crystallisate is filtered with suction and thoroughly washed with cold hexane. The salt is treated with 1N HCl and the acid is extracted with ether. Concentration by evaporation yields 6-cyclohexyl-2(R)-isopropyl-4-hexenoic acid of 90% ee. If the quinine salt is recrystallised a second time from ether/hexane before the treatment with HCl, the (R)-acid obtainable therefrom has a purity of more than 95% ee.

Workup

  1. concentrationThe mixture is concentrated by evaporation
  2. customthe residue is recrystallised from ether hexane
  3. filtrationThe crystallisate is filtered with suction
  4. washthoroughly washed with cold hexane
  5. additionThe salt is treated with 1N HCl
  6. extractionthe acid is extracted with ether
  7. concentrationConcentration
  8. customby evaporation

Sources & evidence

ORD record
ord-76c03f933129434e8d3294d80f005d1c
Source dataset
uspto-grants-1990_02
Patent number
US04898977

Reaction notes

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