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

HRID 640542Notes

Reaction equation

HRID 640542 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-fe60757a47e540a78ef07be4a4b911b4
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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