Ethyl Acetate → (RS)-3-[5-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one

HRID 1900079Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900079
Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:12][CH:11]([CH2:13][O:14][CH3:15])[O:10][C:9]2=[O:16])=[N:6][CH:7]=1.C[Sn](C)(C)[C:19]1[CH2:28][CH2:27][C:22]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:21][CH:20]=1.C(OCC)(=O)C.[F-].[K+]>O1CCCC1.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>[O:23]1[C:22]2([CH2:27][CH2:28][C:19]([C:2]3[CH:3]=[CH:4][C:5]([N:8]4[CH2:12][CH:11]([CH2:13][O:14][CH3:15])[O:10][C:9]4=[O:16])=[N:6][CH:7]=3)=[CH:20][CH2:21]2)[O:26][CH2:25][CH2:24]1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 111741648-Trimethylstannyl-1,4-dioxa-spiro[4,5]dec-7-eneHCID 233718183-(5-Bromo-pyridin-2-yl)-5-methoxymethyl-oxazolidin-2-one

Produkt 1

HCID 23371891(RS)-3-[5-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-oneAusbeute 37,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A suspension of 1.4 g of 3-(5-bromo-pyridin-2-yl)-5-methoxymethyl-oxazolidin-2-one, 1.4 g of 8-trimethylstannyl-1,4-dioxa-spiro[4,5]dec-7-ene and 0.3 of bis(triphenylphosphine)palladium(II) dichloride in 20 ml of tetrahydrofuran was stirred at 70° under argon for 18 h. Then, the mixture was cooled, treated with 150 ml of ethyl acetate and 150 ml of saturated potassium fluoride solution and stirred for 30 minutes. The mixture was filtered over a Celite® pad, the phases were separated and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulfate, concentrated and chromatographed over silica gel 60 with diethyl ether as the eluent. There was obtained 0.6 g of (RS)-3-[5-(1,4-dioxa-spiro[4,5]dec-7-en-8-yl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one. 1H-nmr(CDCl3) ppm: 8.41 (s, 1H), 8.03 (d, 1H), 7.89 (d, 1H), 6.08 (t, 1H), 4.82 (m, 1H), 4.21 (t, 1H), 3.91 (t, 1H), 3.92 (s, 4H), 3.60 (m, 2H), 3.32 (s, 3H), 2.54 (m, 2H), 2.38 (m, 2H), 1.82 (t, 2H).

Aufarbeitung

  1. temperatureThen, the mixture was cooled
  2. stirringstirred for 30 minutes
  3. filtrationThe mixture was filtered over a Celite® pad
  4. customthe phases were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customchromatographed over silica gel 60 with diethyl ether as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-3c7be97ab065488eb9327708844e6e30
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05574055

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