Water → HCID 131721088, compound

HRID 343524Notes

Reaction equation

HRID 343524 reaction equation
[C:1]([C@@:11]([C:28]([OH:30])=[O:29])([OH:27])[C@@:12]([C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)([OH:16])[C:13]([OH:15])=[O:14])(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.O.[Cl:32][C:33]1[CH:34]=[C:35]([C:40]2([CH2:45][CH2:46][OH:47])[CH2:44][CH2:43][NH:42][CH2:41]2)[CH:36]=[CH:37][C:38]=1[Cl:39]>CO>[C:17]([C@@:12]([C:13]([OH:15])=[O:14])([OH:16])[C@@:11]([C:1](=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)([OH:27])[C:28]([OH:30])=[O:29])(=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.[Cl:32][C:33]1[CH:34]=[C:35]([C@:40]2([CH2:45][CH2:46][OH:47])[CH2:44][CH2:43][NH:42][CH2:41]2)[CH:36]=[CH:37][C:38]=1[Cl:39]

Participants

5

Reactant 3

HCID 962Water2×HCID 184644272-(3-(3,4-Dichlorophenyl)pyrrolidin-3-yl)ethanolHCID 66875563HCID 66875563, compound

Product 1

HCID 131721088HCID 131721088, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Combine (S,S)-di-p-anisoyltartaric acid (14.77 g, 35 mmol), water (200 mL) and methanol (200 mL). Heat to reflux. Add dropwise, a solution of 3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine (18.36 g, 70 mmol) in methanol (135 mL). After 1.5 hours, add water (135 mL) and slowly cool to ambient temperature to give a solid. Filter the solid that forms and rinse with water to give the title compound: mp; 201°-202° C. (dec). Analysis by HPLC, as described in Example 3.3.4 indicates an enantiomeric excess of 99.9%, (99.9% ee). [°]2D0 =+17.90°(c=1.00, dimethylsulfoxide).

Workup

  1. temperatureHeat to reflux
  2. additionAdd dropwise
  3. customto give a solid
  4. filtrationFilter the solid that forms
  5. washrinse with water

Sources & evidence

ORD record
ord-6d8b9e7d736a46c790dc161e409b366d
Source dataset
uspto-grants-1999_01
Patent number
US05861417

Reaction notes

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