Tributylstannane → HCID 117701723, compound

HRID 1507454Notes

Reaction equation

HRID 1507454 reaction equation
C([SnH](CCCC)CCCC)CCC.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH2:26]([O:33][C:34]1[C:43]([CH:44](OC(N2C=CN=C2)=S)[C:45]([F:48])([F:47])[F:46])=[C:42]2[C:37]([C:38](=[O:74])[C:39]([CH3:73])=[C:40]([CH:57]3[CH2:62][CH2:61][N:60]([C:63]([O:65][CH2:66][C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)=[O:64])[CH2:59][CH2:58]3)[O:41]2)=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[CH2:26]([O:33][C:34]1[C:43]([CH2:44][C:45]([F:46])([F:47])[F:48])=[C:42]2[C:37]([C:38](=[O:74])[C:39]([CH3:73])=[C:40]([CH:57]3[CH2:62][CH2:61][N:60]([C:63]([O:65][CH2:66][C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)=[O:64])[CH2:59][CH2:58]3)[O:41]2)=[CH:36][CH:35]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 117701561HCID 117701561, compound

Product 1

HCID 117701723HCID 117701723, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tri-n-butyltin hydride (104 μL, 0.39 mmol) and a catalytic amount of azobisisobutyronitrile were added to a solution of benzyl 4-[7-(benzyloxy)-3-methyl-4-oxo-8-{2,2,2-trifluoro-1-[(1H-imidazol-1-ylcarbonothioyl)oxy]ethyl}-4H-chromen-2-yl]piperidine-1-carboxylate (135 mg, 0.20 mmol) obtained in Example 36-3 in tetrahydrofuran (1.5 mL), and the mixture was heated to reflux for 1 hour. The reaction solution was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=80/20→40/60) to obtain 105 mg of the title compound (yield: 95%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=80/20→40/60)

Sources & evidence

ORD record
ord-ecf39e04c44d4584801fa8afa8913497
Source dataset
uspto-grants-2015_12
Patent number
US09221811B2

Reaction notes

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