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

HRID 851400Notes

Reaction equation

HRID 851400 reaction equation
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]

Participants

5

Reactant 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

Product 1

HCID 22823199methyl 2-[(3S,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoateYield 96.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-cea6e7d14a4e4e738914965863aa760c
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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