Sodium Hydroxide → HCID 23371888, Verbindung

HRID 1900053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1900053
O1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[CH:13][C:14]([N:17]4[CH2:21][CH:20]([CH2:22][O:23][CH3:24])[O:19][C:18]4=[O:25])=[N:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4]CC1.[OH-].[Na+]>O1CCCC1.Cl>[CH3:24][O:23][CH2:22][CH:20]1[O:19][C:18](=[O:25])[N:17]([C:14]2[CH:13]=[CH:12][C:11]([CH:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]3)=[CH:16][N:15]=2)[CH2:21]1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 23371867HCID 23371867, Verbindung

Produkt 1

HCID 23371888HCID 23371888, VerbindungAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 0.5 g of (RS)-3-[5-(1,4-dioxa-spiro[4,5]decan-8-yl)-pyridin-2-yl]-5-methoxymethyl-oxazolidin-2-one in 20 ml of tetrahydrofuran and 5 ml of 2N hydrochloric acid was stirred at room temperature for 4 h. Then, 10 ml of 2N sodium hydroxide solution were added and the mixture was extracted several times with ethyl acetate. The organic phases were combined, dried with magnesium sulfate and concentrated. After chromatography with ethyl acetate on silica gel there was obtained 0.4 g of (RS)-5-methoxymethyl-3-[5-(4-oxo-cyclohexyl)-pyridin-2-yl]-oxazolidin-2-one. 1H-nmr (CDCl3) ppm: 8.22 (s, 1H), 8.18 (d,1H), 7.58 (d, 1H), 4.78 (m,1H), 4.27 (t, 1H), 4.09 (t, 1H), 3.64 (m, 2H), 3.43 (s, 3H), 3.08 (m, 1H), 2.51 (m, 4H), 2.04 (bm, 4H).

Aufarbeitung

  1. extractionthe mixture was extracted several times with ethyl acetate
  2. dry with materialdried with magnesium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dcebf407d6c14be3a73f2b43dd0e2480
Quelldatensatz
uspto-grants-1996_11
Patentnummer
US05574055

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