Tetrahydrofuran → (R)-4-methyl-4-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)oxazolidin-2-one

HRID 1036399

Reaktionsgleichung

Reaktionsgleichung von HRID 1036399
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C@:12]1([CH3:18])[CH2:16][O:15][C:14](=[O:17])[NH:13]1)[CH:6]=[CH:5]2.[CH2:19]([CH:24]1[CH2:29][CH2:28][CH:27](O)[CH2:26][CH2:25]1)[CH2:20][CH2:21][CH2:22][CH3:23].O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(OCC)(=O)C>[CH3:18][C@@:12]1([C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([O:1][CH:27]4[CH2:26][CH2:25][CH:24]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:29][CH2:28]4)[CH:3]=3)[CH:8]=2)[CH2:16][O:15][C:14](=[O:17])[NH:13]1

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 410764-PentylcyclohexanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Produkt 1

HCID 67413569(R)-4-methyl-4-(6-(4-pentylcyclohexyloxy)naphthalen-2-yl)oxazolidin-2-oneAusbeute 68,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

(R)-4-(6-Hydroxnaphthalen-2-yl)-4-methyl-oxazolidin-2-one (Example 4, 0.3303 g, 0.001358 mol) was added to a capped 40 mL vial equipped with a magnetic stir bar. 4-Pentyl-cyclohexanol (0.277 g, 0.00163 mol) was added, followed by tetrahydrofuran (6.00 mL, 0.0740 mol). Triphenylphosphine polymer-bound (1.17 g, 0.00217 mol) was then added and the mixture was stirred for 5 minutes. Diisopropyl azodicarboxylate (0.428 mL, 0.00217 mol) was then added and the mixture was stirred for 48 hours at room temperature. The mixture was diluted in ethyl acetate, filtered through CELITE™, concentrated under vacuum and purified by flash chromatography (0-5% MeOH in dichloromethane) to give 0.3672 g of the title compound (68% yield).

Aufarbeitung

  1. customvial equipped with a magnetic stir bar
  2. stirringthe mixture was stirred for 48 hours at room temperature
  3. filtrationfiltered through CELITE™
  4. concentrationconcentrated under vacuum
  5. custompurified by flash chromatography (0-5% MeOH in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-e9105e36287c4fff8baf3f4d99ba2793
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546359B2

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