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

HRID 1601435Notes

Reaction equation

HRID 1601435 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-dffb0ed2701e4b6683d3749a641a83dc
Source dataset
uspto-grants-1999_11
Patent number
US05977139

Reaction notes

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