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

HRID 419515Notes

Reaction equation

HRID 419515 reaction equation
C([O-])(=O)C.[CH2:5]([O:7][C:8]1[CH:9]=[C:10]([C:17]2[CH:22]=[CH:21][N+:20]([CH2:23][CH2:24][CH3:25])=[CH:19][CH:18]=2)[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH3:6].[BH4-].[Na+]>CO.CCOC(C)=O>[CH2:5]([O:7][C:8]1[CH:9]=[C:10]([C:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH3:25])[CH2:19][CH:18]=2)[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH3:6]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 666499234-[3-(Ethyloxy)-4-nitrophenyl]-1-propylpyridinium acetate

Product 1

HCID 594530114-[3-(Ethyloxy)-4-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridineYield 76.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-[3-(ethyloxy)-4-nitrophenyl]-1-propylpyridinium acetate (0.84 g, 2.42 mmol) in 25 mL of MeOH at 0° C. was added, NaBH4 (0.275 g, 7.28 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. NaHCSO3, dried (Na2SO4), filtered, rotovaped down, and purified by flash chromatography to give the title compound of step D (0.536 g, 1.85 mmol, 76%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.80 (d, J=8.61 Hz, 1H), 7.23 (d, J=1.46 Hz, 1H), 7.11 (dd, J=8.42, 1.65 Hz, 1H), 6.37 (t, J=3.57 Hz, 1H), 4.23 (q, J=6.96 Hz, 2H), 3.06 (d, J=3.11 Hz, 2H), 2.58 (t, J=5.59 Hz, 2H), 2.44-2.50 (m, 2H), 2.29-2.35 (m, 2H), 1.41-1.51 (m, J=7.36, 7.36, 7.36, 7.36, 7.36 Hz, 2H), 1.31 (t, J=6.96 Hz, 3H), 0.85 (t, J=7.33 Hz, 3H).

Workup

  1. washwashed with conc. NaHCSO3
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-a3e6260bd71f4659b7d200888e657138
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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