Sodium Acetate → (S)-Cyclopropanecarboxylic acid [1-(4-formyl-phenyl)-ethyl]-amide

HRID 523987

Reaktionsgleichung

Reaktionsgleichung von HRID 523987
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([CH:13]2[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.[C:16]([O-])(=[O:18])C.[Na+]>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH:16]([C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([CH:13]2[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1)=[O:18]

Komponenten

6

Edukt 2

HCID 517045Sodium AcetateHCID 800360N-[(1S)-1-(4-bromophenyl)ethyl]cyclopropanecarboxamide

Produkt 1

HCID 118940157(S)-Cyclopropanecarboxylic acid [1-(4-formyl-phenyl)-ethyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 5.0 g (19 mmol) (S)-cyclopropanecarboxylic acid [1-(4-bromo-phenyl)-ethyl]-amide (WO 2012/01107) in 40 mL MeOH are added 125 mg (0.600 mmol) palladium-(II)-acetate, 620 mg (1.10 mmol) 1,1′-bis(diphenylphosphino)-ferrocene and 4.6 g (56 mmol) sodium acetate. The mixture is stirred at 100° C. and 5 bar CO atmosphere over night. After that time, the mixture is filtered over celite and the filtrate is concentrated by evaporation. The residue is purified by column chromatography (silica gel; gradient hexane/EtOAc 1:0→1:4) to yield the desired product.

Aufarbeitung

  1. wait5 bar CO atmosphere over night
  2. filtrationAfter that time, the mixture is filtered over celite
  3. concentrationthe filtrate is concentrated by evaporation
  4. customThe residue is purified by column chromatography (silica gel; gradient hexane/EtOAc 1:0→1:4)

Quellen und Nachweise

ORD-Eintrag
ord-1979cb4f0c68403c9e15e365b6562dbe
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340510B2

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