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

HRID 1036521

Reaktionsgleichung

Reaktionsgleichung von HRID 1036521
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([OH:12])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].O1CCCC1.O[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([C@:29]1([CH3:35])[CH2:33][O:32][C:31](=[O:34])[NH:30]1)[CH:23]=[CH:22]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[CH3:35][C@@:29]1([C:24]2[CH:23]=[CH:22][C:21]3[C:26](=[CH:27][CH:28]=[C:19]([O:12][CH:9]4[CH2:8][CH2:7][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]4)[CH:20]=3)[CH:25]=2)[CH2:33][O:32][C:31](=[O:34])[NH:30]1

Komponenten

8

Edukt 7

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 410764-PentylcyclohexanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5462977Diethyl azodicarboxylateHCID 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-one

Versuchsvorschrift

In a 40 mL vial, 4-Pentyl-cyclohexanol (1144.4 mg, 0.0067202 mol) was diluted with tetrahydrofuran (30.0 mL, 0.370 mol, Acros) and subsequently (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (1.4924 g, 0.0061350 mol) and triphenylphosphine (2105.5 mg, 0.0080275 mol) were added and the mixture was stirred. Diethyl Azodicarboxylate in toluene (2.6 mL, 0.0086326 mol, Aldrich) was added, and the mixture was then stirred at room temperature for 38 h. The reaction mixture was evaporated to dryness and chromatographed 0-100% EtOAc/Hexanes (adsorbed onto silica gel). Isolated was 0.6142 g (18%) in approx 70% purity, the remainder being reduced DEAD reagent.

Aufarbeitung

  1. additionwere added
  2. stirringthe mixture was then stirred at room temperature for 38 h
  3. customThe reaction mixture was evaporated to dryness
  4. customchromatographed 0-100% EtOAc/Hexanes (adsorbed onto silica gel)
  5. customIsolated

Quellen und Nachweise

ORD-Eintrag
ord-50a3bf3819c54405854819d6f6526ab2
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546359B2

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