Acetic Acid → 2-(4-Fluoro-benzyloxy)-5-(2-nitro-ethyl)-pyridine

HRID 77941Notes

Reaction equation

HRID 77941 reaction equation
CS(C)=O.[F:5][C:6]1[CH:24]=[CH:23][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[N+:20]([O-:22])=[O:21])=[CH:14][N:13]=2)=[CH:8][CH:7]=1.C(O)(=O)C.[BH4-].[Na+]>O>[F:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][N+:20]([O-:22])=[O:21])=[CH:14][N:13]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 592553152-(4-Fluoro-benzyloxy)-5-((E)-2-nitro-vinyl)-pyridine

Product 1

HCID 592554842-(4-Fluoro-benzyloxy)-5-(2-nitro-ethyl)-pyridineYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethyl sulfoxide (20.0 mL) solution of 2-(4-fluoro-benzyloxy)-5-((E)-2-nitro-vinyl)-pyridine (2.60 g, 9.48 mmol) described in Manufacturing Example 58-1-3 and acetic acid (3.00 mL) was added sodium borohydride (574 mg, 15.2 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 20 minutes. Water was then added dropwise at room temperature while cooling appropriately to quench sodium borohydride. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5) to obtain the title compound (785 mg, 30.0%).

Workup

  1. temperaturewhile cooling appropriately under nitrogen atmosphere
  2. temperaturewhile cooling appropriately
  3. customto quench sodium borohydride
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5)

Sources & evidence

ORD record
ord-701ac279f01144b2bebf2575b2549164
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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