Acetone → (-)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid

HRID 323237Notes

Reaction equation

HRID 323237 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.CC(C)=O>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

5

Reactant 3

HCID 180AcetoneHCID 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

Add a hot solution of 3-phenyl-3-(2-hydroxyethyl)pyrrolidine (5.0 g, 20.2 mmol) in ethanol (100 mL) to a refluxing solution of (R,R)-di-p-anisoyltartaric acid (8.46 g, 20.2 mmol), containing a small amount of acetone) in ethanol (200 mL). After the addition is complete, slowly cool to ambient temperature to give a solid. Collect the solid by filtration and recrystallize the solid three times from ethanol to give (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt: mp; 178.0-179.0° C. Elemental Analysis calculated for C12H17NO.C20H18O10: C 63.05; H 5.79; N 2.30; Found: C 62.72; H 5.80; N 2.33. After conversion of a sample to the 3,4,5-trimethoxybenzamide using sodium carbonate and 3,4,5-trimethoxybenzoyl chloride in acetone/water, analysis on HPLC using a CHIRALPAK AD (10 μm×4.6 cm×250 cm) column eluting with pentane/ethanol/methanol/triethylamine (80/15/5/0.1) with a flow rate of 1.5 mL/minute indicates an enantiomeric excess of 99.9%, (99.9% ee), retention time 22.30 minutes for the 3,4,5-trimethoxybenzamide prepared from the (−)-isomer of (R,R)-di-p-anisoyltartaric acid salt.

Workup

  1. additionAfter the addition
  2. customto give a solid
  3. customCollect the solid
  4. filtrationby filtration
  5. customrecrystallize the solid three times from ethanol

Sources & evidence

ORD record
ord-a1f543e60a9c499992f984ab6df774d0
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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