Sodium borohydride → HCID 21961470, compound

HRID 491626Notes

Reaction equation

HRID 491626 reaction equation
[I-].[CH3:2][N+:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:20])([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH3:10])=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[CH3:2][N:3]1[CH2:4][CH:5]=[C:6]([C:9]([CH3:20])([C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)[CH3:10])[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22249345HCID 22249345, compound

Product 1

HCID 21961470HCID 21961470, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Methyl-4-[1-methyl-1-(4-nitro-phenyl)-ethyl]-pyridinium (Step A) was treated with DEA (100 mL) in MeOH (300 mL) for 2 h. NaBH4 (19 g, 500 mmol) was added in small portions. The resulting mixture was stirred for 30 min at RT, then partitioned between CH2Cl2/H2O (500 mL/500 mL). The organic layer was collected and the upper layer was washed with CH2Cl2 (300 mL×3). The combined organic layer was washed with brine then concentrated in vacuo. The residue was purified on a silica washed-column (7% TEA in EtOAc). The desired fractions were combined and concentrated under vacuum to give the desired compound as a dark gray solid. (MS: M+1=261).

Workup

  1. custompartitioned between CH2Cl2/H2O (500 mL/500 mL)
  2. customThe organic layer was collected
  3. washthe upper layer was washed with CH2Cl2 (300 mL×3)
  4. washThe combined organic layer was washed with brine
  5. concentrationthen concentrated in vacuo
  6. customThe residue was purified on a silica washed-column (7% TEA in EtOAc)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-287c66c47afb4147a067f41b38a509ef
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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