Tributylstannane → HCID 19887190, compound

HRID 654406Notes

Reaction equation

HRID 654406 reaction equation
[CH2:1]([N:5]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1)[C:6](=[O:17])[CH:7](Cl)[C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=1)[CH:2]=[CH:3][CH3:4].C([SnH](CCCC)CCCC)CCC.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[CH2:3]([CH:2]1[CH2:1][N:5]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[C:6](=[O:17])[CH:7]1[C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 53802832HCID 53802832, compound

Product 1

HCID 19887190HCID 19887190, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(2-Butenyl)-N-(3-trifluoromethylphenyl)-2-chloro-2-(3,5-difluorophenyl)acetamide (1.6 g) was added to 30 ml of benzene, followed by the addition of 1.1 ml of tributyltin hydride and a catalytic amount of α,α-azobisisobutyronitrile (AIBN) under stirring at the refluxing temperature. The reaction mixture was then stirred for 20 minutes at the refluxing temperature. The reaction mixture was then concentrated in an evaporator. The resultant concentrate was purified by chromatography on a silica gel, whereby 0.75 g of the 3,4-trans isomer of 4-ethyl-3-(3,5-difluorophenyl)-1-(3-trifluoromethylphenyl)-2-pyrrolidinone and 0.14 g of its 3,4-cis isomer were obtained.

Workup

  1. concentrationThe reaction mixture was then concentrated in an evaporator
  2. concentrationThe resultant concentrate
  3. customwas purified by chromatography on a silica gel, whereby 0.75 g of the 3,4-trans isomer of 4-ethyl-3-(3,5-difluorophenyl)-1-(3-trifluoromethylphenyl)-2-pyrrolidinone and 0.14 g of its 3,4-cis isomer
  4. customwere obtained

Sources & evidence

ORD record
ord-386a28b0206b42b8adf262c3bd743bc4
Source dataset
uspto-grants-1992_07
Patent number
US05131947

Reaction notes

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