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Piperidine → HCID 58631179, Verbindung

HRID 525605
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 525605
[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=2)[O:6][C:5]([CH3:16])([CH3:15])[N:4]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[C:24]([Si:26]([CH3:29])([CH3:28])[CH3:27])#[CH:25].N1CCCCC1>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[F:1][CH2:2][C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][C:11]([C:25]#[C:24][Si:26]([CH3:29])([CH3:28])[CH3:27])=[CH:10][CH:9]=2)[O:6][C:5]([CH3:16])([CH3:15])[N:4]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 8082PiperidineHCID 66111TrimethylsilylacetyleneHCID 73424774(4S,5R)-Tert-butyl 4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylate

Produkt 1

HCID 58631179HCID 58631179, VerbindungAusbeute 88,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a toluene (40 ml) solution of (4S,5R)-tert-butyl 4-(fluoromethyl) -5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylate (2.0 g, 4.6 mmols) is added ethynyltrimethylsilane (451 mg, 4.6 mmols), copper (I)iodide (88 mg, 0.46 mmols, 0.1 equivs), Bis(triphenylphosphine)palladium(II) dichloride (165 mg, 0.23 mmols, 0.05 equivs) and piperidine (782 mg, 9.2 mmols, 2 equivs). The mixture is heated in an atmosphere of nitrogen at 35° C. for six hours. The mixture is filtered through a pad of Celite. The pad of Celite is washed with ethylacetate (2×15 ml). The combined organic filtrates were concentrated using rotary evaporation at reduced pressure to give a crude viscous oil. The oil is purified by flash column chromatography (grading from 100% hexanes to 15% EtOAc) to give the title compound (1.65 g): m/z (Cl) 306 ([M+H]+−Boc).

Aufarbeitung

  1. filtrationThe mixture is filtered through a pad of Celite
  2. washThe pad of Celite is washed with ethylacetate (2×15 ml)
  3. concentrationThe combined organic filtrates were concentrated
  4. customevaporation at reduced pressure
  5. customto give a crude viscous oil
  6. customThe oil is purified by flash column chromatography (grading from 100% hexanes to 15% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-789f19dad1e449dbbc1c8cf6332d87e8
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340564B2

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