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

HRID 343520Notes

Reaction equation

HRID 343520 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 acid

Product 1

HCID 70109704(-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Combine 3-phenyl-3-(2-hydroxyethyl)pyrrolidine (101 g, 530 mmol) and ethanol (1.92 L). Heat to reflux. Add a refluxing solution of (R,R)-di-p-anisoyltartaric acid (107 g, 410 mmol) in ethanol (3.9 L). Continue to reflux. After 10 minutes, slowly cool to ambient temperature and add seed crystals. After 18 hours, collect the solid that forms by filtration, rinse with ethanol (200 mL). recrystallize twice from ethanol to give (-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt: mp; 179°-180° C. [α]2D0 =-108.8(c=1.02, methanol).

Workup

  1. temperatureHeat to reflux
  2. temperatureContinue to reflux
  3. additionadd seed crystals
  4. waitAfter 18 hours
  5. customcollect the solid that forms
  6. filtrationby filtration
  7. washrinse with ethanol (200 mL)
  8. customrecrystallize twice from ethanol

Sources & evidence

ORD record
ord-f0df9bb2e14e4a2a94ac1ee4d16ab909
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

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