Sodium borohydride → 4-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridine

HRID 419474Notes

Reaction equation

HRID 419474 reaction equation
[I-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH:18]=[CH:17][N+:16]([CH2:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].[BH4-].[Na+]>CO.CCOC(C)=O>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH3:21])[CH2:15][CH:14]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 666496524-(3-Methoxy-4-nitrophenyl)-1-propylpyridinium iodide

Product 1

HCID 598602684-(3-Methoxy-4-nitrophenyl)-1-propyl-1,2,3,6-tetrahydropyridineYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-[3-(methyloxy)-4-nitrophenyl]-1-propylpyridinium iodide (5.7 g, 14.24 mmol) in 75 mL of MeOH at 0° C. was added, NaBH4 (1.62 g, 42.73 mmol) over 1 h. The mixture was allowed to come to rt over 2 h. The solvent was reduced to approximately 20 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 (3.33 g, 12.05 mmol, 85%). 1H NMR (400 MHz, CDCl3) δ ppm 7.84 (d, J=8.42 Hz, 1H), 7.02 (s, 1H), 6.99-7.02 (m, 1H), 6.19 (ddd, J=3.43, 1.92, 1.79 Hz, 1H), 3.95 (s, 3H), 3.20 (q, J=2.81 Hz, 2H), 2.72 (t, J=5.68 Hz, 2H), 2.54-2.60 (m, 2H), 2.41-2.48 (m, 2H), 1.54-1.64 (m, 2H), 0.94 (t, J=7.42 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-98e2098ad1c344278503f548504f0e6e
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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