2-(3-Phenylpyrrolidin-3-yl)ethanol → (-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid

HRID 1601434Notes

Reaction equation

HRID 1601434 reaction equation
[C:1]1([C:7]2([CH2:12][CH2:13][OH:14])[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([C@:25]([C:42]([OH:44])=[O:43])([OH:41])[C@:26]([C:31](=[O:40])[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)([OH:30])[C:27]([OH:29])=[O:28])(=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1>C(O)C>[C:31]([C@:26]([C:27]([OH:29])=[O:28])([OH:30])[C@:25]([C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)([OH:41])[C:42]([OH:44])=[O:43])(=[O:40])[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1.[C:1]1([C:7]2([CH2:12][CH2:13][OH:14])[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 184645642-(3-Phenylpyrrolidin-3-yl)ethanolHCID 66875417(R, R)-di-p-anisoyltartaric acid2×

Product 1

HCID 70109704(-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acidYield 39.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent4×

Procedure

Combine 3-phenyl-3-(2-hydroxyethyl)pyrrolidine (99.2 g, 659 mmol) and ethanol (2.5 L). Heat to reflux. Add a refluxing solution of (R,R)-di-p-anisoyltartaric acid (212 g, 507 mmol) in ethanol (5.07 L). After the addition is complete, slowly cool to ambient temperature with stirring to give an oil. Dissolve the oil in ethanol at reflux (595 mL) and add a refluxing solution of (R,R)-di-p-anisoyltartaric acid (49.2 g) in ethanol (1.1 L). Cool to ambient temperature with stirring to give a solid. Collect the solid by filtration and recrystallize from ethanol (3.2 L) to give a second solid. Collect the second solid by filtration and recrystallize from ethanol (2.6 L), seed with (-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt to give (-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt (121 g).

Workup

  1. temperatureHeat to reflux
  2. additionAfter the addition
  3. customto give an oil
  4. temperatureat reflux (595 mL)
  5. temperatureCool to ambient temperature
  6. stirringwith stirring
  7. customto give a solid
  8. customCollect the solid
  9. filtrationby filtration
  10. customrecrystallize from ethanol (3.2 L)
  11. customto give a second solid
  12. customCollect the second solid
  13. filtrationby filtration
  14. customrecrystallize from ethanol (2.6 L), seed with (-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt

Sources & evidence

ORD record
ord-9a7a6bb753fc4aa3b4b586b30a123064
Source dataset
uspto-grants-1999_11
Patent number
US05977139

Reaction notes

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