Tributylstannane → (6R,7S)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-1-aza-3-oxabicyclo[4,2,0]-octan-8-one

HRID 851415Notes

Reaction equation

HRID 851415 reaction equation
[CH3:1][C:2]1([CH3:17])[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:16])[C@@:5]2([C:12]([OH:15])([CH3:14])[CH3:13])[N+]#[C-].C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[CH3:1][C:2]1([CH3:17])[O:9][CH2:8][CH2:7][C@H:6]2[N:3]1[C:4](=[O:16])[C@@H:5]2[C:12]([OH:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 53810652(6R,7R)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-7-isocyano-1-aza-3-oxabicyclo[4.2.0]octan-8-one

Product 1

HCID 13194415(6R,7S)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-1-aza-3-oxabicyclo[4,2,0]-octan-8-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of (6R,7R)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-7-isocyano-1-aza-3-oxabicyclo[4.2.0]octan-8-one and its (6R,7S)-isomer (2.5 g) in benzene (75 ml) were added tributyltinhydride (3.07 ml) and azobisisobutyronitrile (170 mg) at ambient temperature and the mixture was refluxed for 30 minutes. The reaction mixture was chromatographed on silica gel (65 g) eluting with a mixture of methylene chloride and acetone (10:1-2:1) to give a crude product, which was purified by silica gel (75 g) chromatography (hexane and ethyl acetate) to give (6R,7S)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-1-aza-3-oxabicyclo[4,2,0]-octan-8-one (0.545 g) [(6R,7S)-isomer] and its (6R,7R)-isomer (1.406 g).

Workup

  1. temperaturethe mixture was refluxed for 30 minutes
  2. customThe reaction mixture was chromatographed on silica gel (65 g)
  3. washeluting with a mixture of methylene chloride and acetone (10:1-2:1)
  4. customto give a crude product, which
  5. customwas purified by silica gel (75 g) chromatography (hexane and ethyl acetate)

Sources & evidence

ORD record
ord-f32dd7674772494da224846f68f6107f
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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