Sodium hydride → (R)-1-(tetrahydrofuran-3-yl)imidazolidin-2-one

HRID 2278952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2278952
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C@@H:8]1[CH2:12][CH2:11][O:10][CH2:9]1)=[O:6].[H-].[Na+]>C1COCC1>[O:10]1[CH2:11][CH2:12][C@@H:8]([N:7]2[CH2:2][CH2:3][NH:4][C:5]2=[O:6])[CH2:9]1

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 90426389(R)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea

Produkt 1

HCID 90427282(R)-1-(tetrahydrofuran-3-yl)imidazolidin-2-oneAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A −20° C. solution of (R)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea (0.522 g, 2.71 mmol) in THF (30 mL) was treated with NaH (60% in mineral oil, 0.130 g, 3.25 mmol) and the mixture stirred at RT overnight as the cooling bath expired. The mixture was treated with satd. NH4Cl, dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford (R)-1-(tetrahydrofuran-3-yl)imidazolidin-2-one (280 mg, 66%). MS (ESI) m/z: 157.1 (M+H+).

Aufarbeitung

  1. additionThe mixture was treated with satd
  2. dry with materialNH4Cl, dried over MgSO4
  3. concentrationconcentrated to dryness
  4. custompurified via silica gel chromatography (MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-4715afd095904ffaa2594630c613c78a
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133183B2

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