Acetic Acid → 2-Benzyl-5-(2-nitro-ethyl)-pyridine

HRID 1691364Notes

Reaction equation

HRID 1691364 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[N+:16]([O-:18])=[O:17])=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BH4-].[Na+]>CS(C)=O>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N+:16]([O-:18])=[O:17])=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 592553902-Benzyl-5-((E)-2-nitro-vinyl)-pyridine

Product 1

HCID 592551352-Benzyl-5-(2-nitro-ethyl)-pyridineYield 22%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 2-benzyl-5-((E)-2-nitro-vinyl)-pyridine (1.2 g, 5.0 mmol) described in Manufacturing Example 210-1-5, acetic acid (300 mg, 5.0 mmol), and dimethyl sulfoxide (10 mL) was added sodium borohydride (94 mg, 2.5 mmol), which was stirred for 10 minutes at room temperature. The reaction solution was partitioned into ethyl acetate and water. The organic layer was separated and passed through a glass filter provided with NH silica gel (eluted with ethyl acetate). The eluate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (260 mg, 22%).

Workup

  1. customThe reaction solution was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. filtrationfilter
  4. customprovided with NH silica gel (eluted with ethyl acetate)
  5. concentrationThe eluate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a6be4e633e714054834fe0d290482efc
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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