Triphenylstannane → HCID 13194414, compound

HRID 1719343Notes

Reaction equation

HRID 1719343 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-].C1([SnH](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.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 6460TriphenylstannaneHCID 6547AzobisisobutyronitrileHCID 18599214(6R,7RS)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-7-isocyano-1-aza-3-oxabicyclo[4.2.0]-octan-8-one

Product 1

HCID 13194414HCID 13194414, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of (6R,7RS)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-7-isocyano-1-aza-3-oxabicyclo[4.2.0]-octan-8-one (920 mg), triphenyltin hydride (1.694 g) and azobisisobutyronitrile (63.4 mg) in benzene (46 ml) was heated at 50° C. for thirty minutes under a nitrogen atmosphere. The mixture was cooled to ambient temperature. The precipitates were filtered off and washed with benzene. The filtrate and washings were combined and chromatographed on silica gel (27.6 g, eluting with 10 to 25% acetone in dichloromethane) to give a crude product mixture, which was re-chromatographed on silica gel (46 g; 230-400 mesh, eluting with a 6:1 to 1:2 mixture of hexane and ethyl acetate) to give 513 mg of (6R,7R)-2,2-dimethyl-7-(1-hydroxy-1-methylethyl)-1-aza-3-oxabicyclo[4.2.0]octan-8-one after crystallization from diisopropyl ether and 170 mg of its 7S isomer as a crystalline solid.

Workup

  1. filtrationThe precipitates were filtered off
  2. washwashed with benzene
  3. customchromatographed on silica gel (27.6 g, eluting with 10 to 25% acetone in dichloromethane)
  4. customto give a crude product mixture, which
  5. customwas re-chromatographed on silica gel (46 g
  6. wash230-400 mesh, eluting with a 6:1 to 1:2 mixture of hexane and ethyl acetate)

Sources & evidence

ORD record
ord-8810b2a410fc446ead6f30464f50d7b9
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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