Triethylamine → HCID 22851231, Verbindung

HRID 1463783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1463783
[CH2:1]([O:8][CH2:9][C@@H:10]([O:13][CH2:14][P:15]([O:21][CH:22]([CH3:24])[CH3:23])([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11]I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[H][H]>CO.[Pd]>[CH2:1]([O:8][CH2:9][C@@H:10]([O:13][CH2:14][P:15]([O:21][CH:22]([CH3:24])[CH3:23])([O:17][CH:18]([CH3:19])[CH3:20])=[O:16])[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 22851228(R)-1-(benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropaneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 22851231HCID 22851231, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of (R)-1-(benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropane (12.0 g, 25.5 mmol) in 15 mL of methanol was treated with triethylamine (3.10 g, 30.6 mmol) and 10% palladium on carbon (2.0 g), and the mixture was placed under 40 psi hydrogen atmosphere in a Parr shaker apparatus. After 2 hours, the reaction mixture was filtered through a 1" pad of Celite, and the collected solid was washed with methanol. The filtrate was concentrated and treated with ethyl acetate (200 mL). The precipitate was removed by filtration, the filtrate was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (10:1, 75% ethyl acetate/hexane) to afford 8.24 g (94%) of the title compound as a clear, colorless oil.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered through a 1" pad of Celite
  2. washthe collected solid was washed with methanol
  3. concentrationThe filtrate was concentrated
  4. additiontreated with ethyl acetate (200 mL)
  5. customThe precipitate was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by column chromatography on silica gel (10:1, 75% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-45a3accc2d784cc7be525a08959560a6
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05302585

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