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Water → (R)-5-Biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-1,5-dihydropyrrol-2-one

HRID 882548
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 882548
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]2[N:12]([C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[C:11](=[O:19])[CH2:10][CH2:9]2)=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1([Se]Br)C=CC=CC=1.O>C1(C)C=CC=CC=1>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]2[N:12]([C:13](=[O:18])[C:14]([CH3:16])([CH3:17])[CH3:15])[C:11](=[O:19])[CH:10]=[CH:9]2)=[CH:5][CH:6]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 123446BromoselenobenzeneHCID 2733832Lithium hexamethyldisilazaneHCID 58160363(S)-5-[(biphenyl-4-yl)methyl]-1-(2,2-dimethylpropionyl)pyrrolidin-2-one

Produkt 1

HCID 59318479(R)-5-Biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-1,5-dihydropyrrol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

1.68 g (S)-5-biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)pyrrolidin-2-one (1, R1=pivaloyl) is added to 10 ml toluene. The mixture is then cooled to −15° C. 5.5 ml Lithium bis(trimethylsilyl)amide (1 M in THF) is then added. After 1 h, a mixture of 1.3 g phenyl selenyl bromide in 10 ml toluene is added. After a further 30 min, 100 ml water is added. The phases are separated and the organic phase concentrated in vacuo. The residue is taken up in 25 ml ethyl acetate and then 5.1 ml hydrogen peroxide (37%) is added at room temperature. After 1 h, the phases are separated and the organic phase washed with a saturated sodium hydrogen carbonate solution and then dried (MgSO4). The mixture is concentrated in vacuo and purified by column chromatography, eluting with heptane/ethyl acetate 5:1 to afford (R)-5-Biphenyl-4-ylmethyl-1-(2,2-dimethylpropionyl)-1,5-dihydropyrrol-2-one. 1H NMR (CDCl3): 1.28 (9H), 2.70 (1H), 3.30 (1H), 4.97 (1H), 5.89 (1H), 7.06 (2H), 7.19 (2H), 7.31 (2H), 7.41 (4H).

Aufarbeitung

  1. additionis added
  2. waitAfter a further 30 min
  3. customThe phases are separated
  4. concentrationthe organic phase concentrated in vacuo
  5. addition5.1 ml hydrogen peroxide (37%) is added at room temperature
  6. waitAfter 1 h
  7. customthe phases are separated
  8. washthe organic phase washed with a saturated sodium hydrogen carbonate solution
  9. dry with materialdried (MgSO4)
  10. concentrationThe mixture is concentrated in vacuo
  11. custompurified by column chromatography
  12. washeluting with heptane/ethyl acetate 5:1

Quellen und Nachweise

ORD-Eintrag
ord-10bde7a098e941de8870265e790acb07
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08993785B2

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