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

HRID 851376Notes

Reaction equation

HRID 851376 reaction equation
N(C(C)(C)C#N)=NC(C)(C)C#N.C([SnH](CCCC)CCCC)CCC.[N+]([C@@H:28]1[C@@H:31]([CH2:32][CH:33]=[CH2:34])[N:30]([C:35](=[C:40]([CH3:42])[CH3:41])[C:36]([O:38][CH3:39])=[O:37])[C:29]1=[O:43])#[C-]>C1C=CC=CC=1>[O:43]=[C:29]1[CH2:28][C@@H:31]([CH2:32][CH:33]=[CH2:34])[N:30]1[C:35](=[C:40]([CH3:42])[CH3:41])[C:36]([O:38][CH3:39])=[O:37]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 54071546methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

Product 1

HCID 54326273methyl 2-[(4R)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoateYield 99.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2,2'-Azobis(2-methylpropionitrile) (98 mg) and tributyltin hydride (0.95 ml) were added to a solution of methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (740 mg) in benzene (15 ml), and the mixture was refluxed for 20 minutes. The reaction mixture was chromatographed on silica gel (15 g) eluting with a mixture of hexane and ethyl acetate (5:1-3:1) to give methyl 2-[(4R)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (660 mg).

Workup

  1. temperaturethe mixture was refluxed for 20 minutes
  2. customThe reaction mixture was chromatographed on silica gel (15 g)
  3. washeluting with a mixture of hexane and ethyl acetate (5:1-3:1)

Sources & evidence

ORD record
ord-d498c1ce26ed402e8eb9dc8c87275523
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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