Sodium cyanoborohydride → HCID 59441903, compound

HRID 1014185Notes

Reaction equation

HRID 1014185 reaction equation
[I-].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N+:12]([CH2:16][CH2:17][CH3:18])[CH:13]=[CH:14][CH:15]=2)=[CH:6][C:5]=1[N+:19]([O-:21])=[O:20].[BH3-]C#N.[Na+]>CO>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH:15]=2)=[CH:6][C:5]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 67317167HCID 67317167, compound

Product 1

HCID 59441903HCID 59441903, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[4-(methyloxy)-3-nitrophenyl]-1-propylpyridinium iodide (6.10 g, 15.22 mmol) in methanol (100 mL) was added NaBH3CN (9.58 g, 152.06 mmol, Aldrich) and the reaction was allowed to stir overnight at rt. The reaction was quenched with water (50 mL), solvent removed under reduced pressure, aqueous layer extracted with dichloromethane (2×50 mL), organic layers combined, taken to a residue under reduced pressure, and purified by column chromatography on SiO2 to provide 5-[4-(methyloxy)-3-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine (1.89 g, 45% over two steps). ESIMS (M+H)+=277.

Workup

  1. customThe reaction was quenched with water (50 mL), solvent
  2. customremoved under reduced pressure, aqueous layer
  3. extractionextracted with dichloromethane (2×50 mL), organic layers
  4. custompurified by column chromatography on SiO2

Sources & evidence

ORD record
ord-febdeb76b02d4372ade36f5c7511cb83
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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