2,3,3-Trimethylbut-1-ene → HCID 178461769, Verbindung

HRID 962301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 962301
C=C(C)C(C)(C)C.CC(C)(C)C(=O)ON(Cc1ccccc1)Cc1ccccc1>C1CCOC1.CC(=O)[O-].CC(=O)[O-].CO[Si](C)OC.COc1c(C(C)(C)C)cc(P(c2cc(C(C)(C)C)c(OC)c(C(C)(C)C)c2)c2ccc3c(c2-c2c(P(c4cc(C(C)(C)C)c(OC)c(C(C)(C)C)c4)c4cc(C(C)(C)C)c(OC)c(C(C)(C)C)c4)ccc4c2OCO4)OCO3)cc1C(C)(C)C.[Cu+2].c1ccc(P(c2ccccc2)c2ccccc2)cc1>C[C@@H](CN(Cc1ccccc1)Cc1ccccc1)C(C)(C)C

Komponenten

8

Edukt 2

HCID 116692,3,3-Trimethylbut-1-eneHCID 142744676(Dibenzylamino) 2,2-dimethylpropanoate

Produkt 1

HCID 178461769HCID 178461769, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 6329250Dimethoxy(methyl)siliconReagenzHCID 8895Cupric acetateKatalysatorHCID 11776TriphenylphosphineKatalysatorHCID 111941924,4'-Bi-1,3-benzodioxole-5,5'-diylbis{bis[4-methoxy-3,5-bis(2-methyl-2-propanyl)phenyl]phosphine}KatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C
Sonstiges
After dropwise addition of dimethoxy(methyl)- silane into reaction mixture in water bath, the vessel was removed and allowed to stir for an additional 12 hours

Aufarbeitung

  1. temperatureKeine Vorschrift aufgezeichnet
  2. additionKeine Vorschrift aufgezeichnet
  3. additionKeine Vorschrift aufgezeichnet
  4. additionKeine Vorschrift aufgezeichnet
  5. additionKeine Vorschrift aufgezeichnet
  6. extraction3 x 50 mL ethyl acetate extraction using a 250-mL separatory funnel · organic-Phase beibehalten
  7. concentrationrotary evaporator (35 degC, 50 mmHg)
  8. flash chromatographySilica (30 g) is added to the crude reaction mixture and the solvent removed in vacuo. This mixture is loaded onto a column, with interior diameter of roughly 2 inches, packed with silica (200 g, SiliCycle, F60/230-400 mesh) and equilibrated with hexanes. The column is eluted under air pressure with 1% ethyl acetate in hexanes (2500 mL). During elution, fractions are collected in test tubes (roughly 28 mL each), and the desired product typically elutes around fractions 13 through 72 (Rf = 0.34). The fractions that contain the product are combined.
  9. concentrationrotary evaporator (30 degC, 80 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-e5c44ec1b5164f8ea077cf3b7ee0214a
Quelldatensatz
Copper-Catalyzed Enantioselective Hydroamination of Alkenes
Originallink
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