1-(Phenylmethyl)-2,5-pyrrolidinedione → HCID 58504592, Verbindung

HRID 2367229

Reaktionsgleichung

Reaktionsgleichung von HRID 2367229
[C:1]1([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]1([Mg]Br)[CH2:17][CH2:16]1>C1COCC1>[CH:15]1([C:12]2([OH:13])[N:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:9](=[O:14])[CH2:10][CH2:11]2)[CH2:17][CH2:16]1

Komponenten

4

Edukt 2

HCID 952411-(Phenylmethyl)-2,5-pyrrolidinedioneHCID 178418630HCID 178418630, Verbindung

Produkt 1

HCID 58504592HCID 58504592, VerbindungAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 1-(phenylmethyl)-2,5-pyrrolidinedione (1 g, 5.29 mmol) in THF (50 mL) at −78° C. was added cyclopropylmagnesium bromide (42.3 mL, 21.1 mmol) dropwise. The reaction mixture was allowed to warm to 0° C. and stirred for an additional 2 hours. The reaction was quenched with a saturated aqueous solution of ammonium chloride and transferred to a separatory funnel. EtOAc was added, and the organic phase was separated. The aqueous layer was further extracted with EtOAc, and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% hexanes to 80% EtOAc/hexanes) afforded the title compound (400 mg, 33%) as a yellow solid. LC-MS (ES) m/z=232 [M+H]+.

Aufarbeitung

  1. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride
  2. customtransferred to a separatory funnel
  3. additionEtOAc was added
  4. customthe organic phase was separated
  5. extractionThe aqueous layer was further extracted with EtOAc
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ae820360a90240069134d3d173d5b4f2
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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