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Benzophenone imine → HCID 86653294, Verbindung

HRID 1187772
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1187772
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[C@H:11]([CH3:22])[O:10][C:9]1([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25]1([C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[NH:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([N:32]=[C:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:17][CH:16]=2)[C@H:11]([CH3:22])[O:10][C:9]1([CH3:24])[CH3:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 67151671HCID 67151671, Verbindung

Produkt 1

HCID 86653294HCID 86653294, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of (4S,5S)-4-[2-(4-bromo-phenyl)-ethyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (3.13 g) in toluene (30 ml) were added diphenylmethanimine (1.71 g) and sodium tert-butoxide (1.06 g). The reaction mixture was degassed by bubbling argon through the mixture for several minutes. BINAP (489 mg) and Pd2(dba)3 (216 mg) were then added and the reaction mixture was stirred at 100° C. for 20 h. The reaction mixture was then cooled to room temperature, poured into EtOAc, and extracted with water. The organic layer was separated, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, gradient: 0% to 30% EtOAc in hexane) to afford (4S,5S)-4-{2-[4-(benzhydrylidene-amino)-phenyl]-ethyl}-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester as a yellow oil (3.2 g, 82%). MS (ISP): 499.3 ([M+H).

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. customby bubbling argon through the mixture for several minutes
  3. additionBINAP (489 mg) and Pd2(dba)3 (216 mg) were then added
  4. temperatureThe reaction mixture was then cooled to room temperature
  5. additionpoured into EtOAc
  6. extractionextracted with water
  7. customThe organic layer was separated
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by flash chromatography (silica gel, gradient: 0% to 30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5702f4b538e54ebb92ac9f088d7d22a9
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673950B2

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