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Tetrahydrofuran → HCID 12800412, Verbindung

HRID 543556
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 543556
[CH:1](NC1CCCCC1)([CH3:3])[CH3:2].C([Li])CCC.[CH2:16]([CH:19]1[N:22]([C:23]([C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:44])=[P:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21](=[O:53])[CH2:20]1)[CH:17]=[CH2:18].[O:54]1CCCC1>CCCCCC>[CH2:16]([CH:19]1[N:22]([C:23]([C:43]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:44])=[P:24]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:21](=[O:53])[CH:20]1[C:1]([OH:54])([CH3:3])[CH3:2])[CH:17]=[CH2:18]
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Komponenten

6

Edukt 4

HCID 8028Tetrahydrofuran2×HCID 62386CyclohexylisopropylamineHCID 127969694-Allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-oneHCID 178418339Butyllithium

Produkt 1

HCID 12800412HCID 12800412, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058
Hexane
Lösungsmittel

Versuchsvorschrift

A solution of N-isopropylcyclohexylamine (0.60 g) in dry tetrahydrofuran (10 cm3) was stirred under argon and cooled to -78°. This was treated with a 2.5 M solution of n-butyl lithium in n-hexane (1.70 cm3). After ten minutes, a solution of 4-allyl-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl) azetidin-2-one (1.00 g) in dry tetrahydrofuran (15 cm3) was added. Five minutes were allowed for the formation of the C(3) carbanion which was then quenched by the addition of dry acetone (0.71 cm3). The cooling bath was then removed and the mixture stirred for a further ten minutes before it was neutralised with acetic acid (0.56 g). The solvent was evaporated under reduced pressure and the residue chromatographed on silica gel 60 (<230 mesh), eluting with ethyl acetate/60°-80° petroleum ether mixtures grading from 1:1 to 7:3. this gave the two separate isomers of 4-allyl-3-(2-hydroxyprop-2-yl)-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one(0.30 g 27%) and (0.22 g, 20%); νmax (CHCl3) 3000, 1735 and 1620 cm-1.

Aufarbeitung

  1. temperaturecooled to -78°
  2. waitAfter ten minutes
  3. customFive minutes
  4. customwas then quenched by the addition of dry acetone (0.71 cm3)
  5. customThe cooling bath was then removed
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue chromatographed on silica gel 60 (<230 mesh)
  8. washeluting with ethyl acetate/60°-80° petroleum ether
  9. customthis gave the two
  10. customseparate isomers of 4-allyl-3-(2-hydroxyprop-2-yl)-1-(1-benzyloxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one(0.30 g 27%) and (0.22 g, 20%)

Quellen und Nachweise

ORD-Eintrag
ord-87e9a1eb450045e28b13eda5c7f213d8
Quelldatensatz
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04446146

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