1-Phenyl-2-pyrrolidin-1-ylethanol → HCID 7195215, compound

HRID 1715867Notes

Reaction equation

HRID 1715867 reaction equation
C(OC(=O)[C@@H]([C@H](C(OC(=O)C1C=CC=CC=1)=O)O)O)(=O)C1C=CC=CC=1.[C:27]1([CH:33]([OH:40])[CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CO.[OH-].[Na+]>[C:27]1([C@@H:33]([OH:40])[CH2:34][N:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 2212131-Phenyl-2-pyrrolidin-1-ylethanolHCID 12858288di-O-benzoyl-L-tartaric acid

Product 1

HCID 7195215HCID 7195215, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 14798Sodium HydroxideSolvent

Procedure

Solutions of 35.8 g of di-O-benzoyl-L-tartaric acid in 150 ml methanol and 19.1 g of 1-phenyl-2-(1-pyrrolidinyl)-ethanol in 100 ml of methanol were mixed and the mixture left standing in a refrigerator for 2 days. The crystalline product was filtered off, washed with a small amount of cold methanol and diethyl ether and dried. The product was repeatedly recrystallised from hot ethanol, yielding an optically pure diastereomeric salt of 15.0 g. The free base was released by dissolving the salt in 100 ml of cold 20% aqueous sodium hydroxide and extracted in dichloromethane. After evaporation of the solvent, 7.2 g (38% based on the starting racemate) of the oily (R)-enantiomer of 1-phenyl-2-(1-pyrrolidinyl)-ethanol were obtained which solidified after storage in a refrigerator to become a crystalline mass. The product had a [αD20] value of −40° (methanol).

Workup

  1. waitthe mixture left
  2. filtrationThe crystalline product was filtered off
  3. washwashed with a small amount of cold methanol and diethyl ether
  4. customdried
  5. customThe product was repeatedly recrystallised from hot ethanol
  6. customyielding an optically pure diastereomeric salt of 15.0 g
  7. extractionextracted in dichloromethane
  8. customAfter evaporation of the solvent, 7.2 g (38%
  9. customwere obtained which

Sources & evidence

ORD record
ord-17990049b1de442283f5c14201e7355e
Source dataset
uspto-grants-2010_09
Patent number
US07799952B2

Reaction notes

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