Citric Acid → (S)-4-(3-Hydroxy-2-methyl-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one

HRID 458026

Reaktionsgleichung

Reaktionsgleichung von HRID 458026
C[O:2][C:3](=O)[CH:4]([CH3:20])[CH2:5][C@H:6]1[CH2:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH2:7]1.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.O>CCO>[OH:2][CH2:3][CH:4]([CH3:20])[CH2:5][C@@H:6]1[CH2:7][N:8]([C@H:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:13])[C:9](=[O:11])[CH2:10]1

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 590940382-Methyl-3-[(S)-5-oxo-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-yl]-propionic Acid Methyl Ester

Produkt 1

HCID 59093973(S)-4-(3-Hydroxy-2-methyl-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-oneAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the ester 93 (4.82 g, 0.017 mol) in EtOH (100 mL) was added NaBH4 (3.7 g, 0.10 mol) and the mixture heated to reflux for 2.5 hours. The solution was cooled to 0° C. and 1 M citric acid carefully added followed by water. The solution was concentrated to half volume added and extracted with ether. The combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/acetone) of the residue gave the product as an oil (2.6 g, 59%). MS m/z 262 (M+H, 100%).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2.5 hours
  3. concentrationThe solution was concentrated to half volume
  4. additionadded
  5. extractionextracted with ether
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-de5ca674164a484b9cbad86585bbcd12
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189747B2

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