Tributylstannane → methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

HRID 1719305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1719305
C([SnH](CCCC)CCCC)CCC.[OH:14][C:15]([C@:18]1([N+]#[C-])[C@@H:21]([CH2:22][CH:23]=[CH2:24])[N:20]([C:25](=[C:30]([CH3:32])[CH3:31])[C:26]([O:28][CH3:29])=[O:27])[C:19]1=[O:33])([CH3:17])[CH3:16].N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[OH:14][C:15]([C@@H:18]1[C@@H:21]([CH2:22][CH:23]=[CH2:24])[N:20]([C:25](=[C:30]([CH3:32])[CH3:31])[C:26]([O:28][CH3:29])=[O:27])[C:19]1=[O:33])([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 53962359methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

Produkt 1

HCID 22823199methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoateAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Tributyltin hydride (0.707 ml) was added to a mixture of methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (630 mg) and azobisisobutyronitrile (34 mg) in benzene (6 ml) at room temperature, and the mixture was refluxed for 15 minutes. The reaction mixture was cooled and chromatographed on silica gel (20 g) eluting with a mixture of hexane and ethyl acetate (3:1-1:1) to give a 3:1 mixture (559 mg) of methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate and its (3R,4R)-isomer.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 15 minutes
  2. temperatureThe reaction mixture was cooled
  3. customchromatographed on silica gel (20 g)
  4. washeluting with a mixture of hexane and ethyl acetate (3:1-1:1)

Quellen und Nachweise

ORD-Eintrag
ord-2572f6797bce49bf80c6ea2d6f575237
Quelldatensatz
uspto-grants-1985_09
Patentnummer
US04539152

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