Methanol → N-[(1S)-1-(3-Fluorophenyl)-3-hydroxypropyl]acetamide

HRID 23933Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 23933
[C:1]([NH:4][C@H:5]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH2:6][C:7](OCC)=[O:8])(=[O:3])[CH3:2].[BH4-].[Na+].CO.[OH-].[Na+]>C1COCC1.O>[F:18][C:14]1[CH:13]=[C:12]([C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:6][CH2:7][OH:8])[CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 59985529Ethyl (3S)-3-(acetamido)-3-(3-fluorophenyl)propanoate

Produkt 1

HCID 59985487N-[(1S)-1-(3-Fluorophenyl)-3-hydroxypropyl]acetamideAusbeute 99,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A stirred suspension of ethyl (3S)-3-(acetylamino)-3-(3-fluorophenyl)propanoate (2.5 g, 9.9 mmol) and sodium borohydride (0.76 g, 20 mmol) in THF (20 ml) was heated at 50° C. under a nitrogen atmosphere. Methanol (1.8 ml) was then carefully added dropwise and the reaction mixture heated under reflux for one hour. The reaction was allowed to cool to room temperature then water (10 ml) and aqueous sodium hydroxide solution (1.5 g NaOH in 4 ml water) carefully added dropwise. The solution was extracted with ethyl acetate (3×30 ml) and the combined organic extracts dried (MgSO4) and evaporated to give the title compound as a white solid (2.08 g).

Aufarbeitung

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for one hour
  3. temperatureto cool to room temperature
  4. extractionThe solution was extracted with ethyl acetate (3×30 ml)
  5. dry with materialthe combined organic extracts dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b938b617d55643e6a1c0f08442a3f1b6
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855724B2

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