1-(Triphenylphosphoranylidene)acetone → 1-(N-Cbz-2-pyrrolidinyl)-1-buten-3-one

HRID 440096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 440096
[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)=[CH:25][C:26](=[O:28])[CH3:27])C=CC=CC=1>C1C=CC=CC=1>[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][CH:12]1[CH:13]=[CH:25][C:26](=[O:28])[CH3:27])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Komponenten

4

Edukt 2

HCID 150381-(Triphenylphosphoranylidene)acetoneHCID 11746545(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 572702461-(N-Cbz-2-pyrrolidinyl)-1-buten-3-oneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a stirred solution of N-Cbz-L-prolinal (6.3 g, 27 mmol, from step 24d above) in 30 mL of benzene was added 9.42 g (29.6 mmol) of 1-triphenylphosphoranylidene-2-propanone (Aldrich) at room temperature. The reaction mixture was heated to reflux for 4 hr. The benzene was removed under vacuum, and the residue was dissolved in ether and cooled for 16 hr. The phosphine oxide by product was removed by filtration, and the solution was further purified by column chromatography on silica gel, eluting with 20% ethyl acetate in hexanes, to afford 4.4 g of the title product (69% yield).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hr
  3. customThe benzene was removed under vacuum
  4. dissolutionthe residue was dissolved in ether
  5. temperaturecooled for 16 hr
  6. customThe phosphine oxide by product was removed by filtration
  7. customthe solution was further purified by column chromatography on silica gel
  8. washeluting with 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-fd7d853d1ad9403c8c3b1b2c8e4ceed7
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516912

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