Propargyl alcohol → HCID 178463301, Verbindung

HRID 1527791Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527791
Br[C:2]1[CH:3]=[C:4]([N:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH3:23])[CH2:18][CH2:17]2)[CH2:14][CH3:15])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(NC(C)C)(C)C.[CH2:38]([OH:41])[C:39]#[CH:40]>C1(C)C=CC=CC=1.[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.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:27]([O:26][C:24]([N:22]([CH3:23])[C@H:19]1[CH2:20][CH2:21][C@H:16]([N:13]([CH2:14][CH3:15])[C:4]2[C:5]([CH3:12])=[C:6]([CH:11]=[C:2]([C:40]#[C:39][CH2:38][OH:41])[CH:3]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:17][CH2:18]1)=[O:25])([CH3:28])([CH3:29])[CH3:30]

Komponenten

8

Edukt 3

HCID 7859Propargyl alcoholHCID 7912DiisopropylamineHCID 178463214HCID 178463214, Verbindung

Produkt 1

HCID 178463301HCID 178463301, VerbindungAusbeute 63,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11776TriphenylphosphineKatalysatorHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of methyl 5-bromo-3-(((trans)-4-((tert-butoxycarbonyl)(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (2 g, 4.14 mmol) in dry toluene was added CuI (0.015 g, 0.079 mmol), PPh3 (0.043 g, 0.165 mmol), PdCl2(PPh3)2 (0.058 g, 0.082 mmol), N,N-diisopropyl amine (1.08 g, 10.78 mmol) and reaction was purged with argon for 15 min. prop-2-yn-1-ol (0.46 g, 8.29 mmol) was added to it reaction was heated at 80° C. at sealed condition for 5 h. On completion, it was quenched with water and extracted with ethyl acetate. Organic layer was dried over Na2SO4. The crude compound was purified by column chromatography to afford the title compound (1.2 g, 63.2% yield).

Aufarbeitung

  1. additionwas added to it reaction
  2. customat sealed condition for 5 h
  3. customOn completion, it was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialOrganic layer was dried over Na2SO4
  6. customThe crude compound was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-380c2542c6ba42a2b107fad4252854c5
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09089575B2

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