DL-Ephedrine → Ephedrine

HRID 2295341Notes

Reaction equation

HRID 2295341 reaction equation
[CH3:1][CH:2]([NH:11][CH3:12])[CH:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.FC1C=CC2S(=O)C3C=C(C(O)=O)C=CC=3C=CC=2C=1>C(O)C>[CH3:1][C@H:2]([NH:11][CH3:12])[C@H:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 5032DL-EphedrineHCID 178524101HCID 178524101, compound

Product 1

HCID 9294Ephedrine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 5 liter flask containing ethanol (3.4 liters) is introduced 1-ephedrine (143.2 g.; 0.868 mole). Racemic 8-fluorodibenzo[b,f]thiepin-3-carboxylic acid-5-oxide (250 g.; 0.868 mole) is added rapidly to this solution and brought to reflux. After the addition, the reflux is continued until complete solution is obtained. The resulting solution is then left at room temperature overnight. The crystals are filtered, washed with a small volume of ethanol and air dried to yield the ephedrine salt of the title product having an enantiomeric purity of 93% (134.2 g.; 68%).

Workup

  1. temperatureto reflux
  2. additionAfter the addition
  3. customis obtained
  4. filtrationThe crystals are filtered
  5. washwashed with a small volume of ethanol and air
  6. customdried

Sources & evidence

ORD record
ord-92f7a3076dd442afa6c86bb2282a8a8b
Source dataset
uspto-grants-1984_01
Patent number
US04424355

Reaction notes

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