Acetic Acid → 4-(2-Pyridin-2-yl-ethyl)-(2-nitro-ethyl)-benzene

HRID 78069Notes

Reaction equation

HRID 78069 reaction equation
O1CCCC1.CS(C)=O.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[N+:26]([O-:28])=[O:27])=[CH:20][CH:19]=1.C(O)(=O)C.[BH4-].[Na+]>O>[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][N+:26]([O-:28])=[O:27])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 21830753dimethylsulfoxide THFHCID 592553604-(2-Pyridin-2-yl-ethyl)-((E)-2-nitrovinyl)-benzene

Product 1

HCID 592553194-(2-Pyridin-2-yl-ethyl)-(2-nitro-ethyl)-benzeneYield 74.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed tetrahydrofuran-dimethyl sulfoxide (1:1) solution of 4-(2-pyridin-2-yl-ethyl)-((E)-2-nitro-vinyl)-benzene (2.83 g, 11.1 mmol) described in Manufacturing Example 93-1-6 and acetic acid (3 mL) was added sodium borohydride (630 mg, 16.7 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 15 minutes at room temperature. Water was added dropwise into this reaction mixture at room temperature while cooling appropriately. The reaction mixture was partitioned into water and ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate: heptane=1:9 then 2:8) to obtain the title compound (2.11 g, 74%).

Workup

  1. temperaturewhile cooling appropriately under nitrogen atmosphere
  2. temperaturewhile cooling appropriately
  3. customThe reaction mixture was partitioned into water and ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-371aefb0737d42c58ccce35bad175d94
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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