Sodium borohydride → HCID 58790390, compound

HRID 418721Notes

Reaction equation

HRID 418721 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[O:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][C:23]=3[F:31])[CH:13]=2)[CH:9]=[CH:10][CH:11]=1.[BH4-].[Na+]>O.O.O.O.O.O.[Ni](Cl)Cl.CO.C1COCC1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]2[S:20][C:19]3[C:14](=[N:15][CH:16]=[CH:17][C:18]=3[O:21][C:22]3[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][C:23]=3[F:31])[CH:13]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58790382HCID 58790382, compound

Product 1

HCID 58790390HCID 58790390, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 11791229Dichloronickel;hexahydrateCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To the nitro compound 364 (0.84 g, 1.8 mmol) and nickel chloride hexahydrate (0.87 g, 3.7 mmol) in 9:1 MeOH/THF was added sodium borohydride (0.30 g, 7.9 mmol) in small portions. The resulting mixture was stirred at r.t. for 1 h, then filtered through celite and concentrated. The residue was partitioned between water and dichloromethane, the organic phase was collected, washed with brine, dried (anhydrous MgSO4), filtered, and concentrated. The residue was purified by flash chromatography (eluent 90% ethyl acetate/hexanes) to afford 365 (0.43 g, 54% yield). LRMS (M+H): 429.1.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated
  3. customThe residue was partitioned between water and dichloromethane
  4. customthe organic phase was collected
  5. washwashed with brine
  6. dry with materialdried (anhydrous MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography (eluent 90% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-60425725161f4e7191d895d6f1d302b7
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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