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

HRID 1786722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786722
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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 7195215HCID 7195215, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel3×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ff18a2aec00d4640b92b602960780621
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507827B2

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