Sodium borohydride → 4-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine

HRID 419522Notes

Reaction equation

HRID 419522 reaction equation
[I-].[CH3:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][N+:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[CH3:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH3:13])=[CH:5][C:4]=1[C:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH:15]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 666497594-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propylpyridinium iodide

Product 1

HCID 594529274-[2-Methyl-5-(methyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridineYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-[2-methyl-5-(methyloxy)-4-nitrophenyl]-1-propylpyridinium iodide (1.04 g, 2.51 mmol) in 25 mL of MeOH at 0° C. was added, NaBH4 (0.284 g, 7.53 mmol) over 1 h. The mixture was allowed to come to rt over 2 h. The solvent was reduced to approximately 5 mL and then diluted with EtOAc, washed with conc. NaHCO3, dried (Na2SO4), filtered, rotovaped down, and purified by flash chromatography to give the title compound of step C (0.7 g, 2.41 mmol, 96%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.71 (s, 1H), 7.00 (s, 1H), 5.61-5.67 (m, 1H), 3.87 (s, 3H), 2.98-3.07 (m, 2H), 2.60 (t, J=5.50 Hz, 2H), 2.28-2.37 (m, 4H), 2.20 (s, 3H), 1.43-1.53 (m, 2H), 0.87 (t, J=7.52 Hz, 3H).

Workup

  1. washwashed with conc. NaHCO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-e1b6302e8efe401ea84425c03e39d657
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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