Tetrahydrofuran → (R)-4-(6-(4,4-dimethylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one

HRID 1036409

Reaktionsgleichung

Reaktionsgleichung von HRID 1036409
[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.O[C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[CH:17]=[C:16]([C@:21]1([CH3:27])[CH2:25][O:24][C:23](=[O:26])[NH:22]1)[CH:15]=[CH:14]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>CC(=O)OCC>[CH3:1][C:2]1([CH3:9])[CH2:7][CH2:6][CH:5]([O:8][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH:17]=[C:16]([C@:21]2([CH3:27])[CH2:25][O:24][C:23](=[O:26])[NH:22]2)[CH:15]=[CH:14]3)[CH2:4][CH2:3]1

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 136735Cyclohexanol, 4,4-dimethyl-HCID 51066623(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one

Produkt 1

HCID 67414756(R)-4-(6-(4,4-dimethylcyclohexyloxy)naphthalen-2-yl)-4-methyloxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 4,4-Dimethylcyclohexanol (63.2 mg, 0.000493 mol), (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyl-oxazolidin-2-one (100 mg, 0.0004 mol), triphenylphosphine (129 mg, 0.000493 mol), and tetrahydrofuran (4 mL, 0.05 mol), diisopropyl azodicarboxylate (0.0971 mL, 0.000493 mol) was added dropwise and was stirred at room temperature overnight. The mixture was diluted with EA and washed with 5% citric acid and brine then dried with magnesium sulfate and concentrated. The crude was taken up into DCM and subjected to ISCO combiflash purification with EtOAc/hexane (0-70) to give product.

Aufarbeitung

  1. additionwas added dropwise
  2. washwashed with 5% citric acid and brine
  3. dry with materialthen dried with magnesium sulfate
  4. concentrationconcentrated
  5. customsubjected to ISCO combiflash purification with EtOAc/hexane (0-70)
  6. customto give product

Quellen und Nachweise

ORD-Eintrag
ord-f596cea7211341bfb4f59d8cbd5f546d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546359B2

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