Hydrochloric Acid → HCID 131723018, compound

HRID 2269852Notes

Reaction equation

HRID 2269852 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.Cl.[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]>O.CO.CO>[ClH:32].[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 184644272-(3-(3,4-Dichlorophenyl)pyrrolidin-3-yl)ethanolHCID 66875417(R, R)-di-p-anisoyltartaric acid

Product 1

HCID 131723018HCID 131723018, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Combine (R, R)-di-p-anisoyltartaric acid (0.8 g, 19 mmol) and aqueous 12 M hydrochloric acid solution (0.16 mL, 19 mmol) in water/methanol (10 mL)/(10 mL). Heat to reflux. Add dropwise, a solution of 3-(3,4-dichloro-phenyl)-3-(2-hydroxy-ethyl)-pyrrolidine (1.0 g, 38.5 mmol) in methanol (10 mL). After 15 minutes, slowly cool to ambient temperature. Filter the solid that forms and rinse with water to give (+)-3-(3,4-dichloro-phenyl)-3-(2-hydroxy-ethyl)-pyrrolidine (R, R)-di-p-anisoyltartaric acid-hydrochloric acid salt: mp; 201-204° C. (dec). Analysis by HPLC, as described in Example 14.1.1 indicates an enantiomeric excess of 97%, (97% ee).

Workup

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

Sources & evidence

ORD record
ord-711ca9fd0918488f9036d09d9a4528fb
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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