Sodium borohydride → HCID 44610348, compound

HRID 1432515Notes

Reaction equation

HRID 1432515 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]1[CH3:18].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]1[N:12]([CH3:18])[CH2:13][CH2:14][C:15]([CH3:17])=[CH:16]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 44610346HCID 44610346, compound

Product 1

HCID 44610348HCID 44610348, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-(2,4-dimethoxyphenyl)-1,4-dimethyl-1,2-dihydropyridine (4) (0.48 g, 2.06 mmol) in methanol (5 ml) at room temperature was added sodium borohydride (98 mg, 2.51 mmol), gas evolution commenced immediately, the resulting mixture was stirred for 3 hours. At this time the solvent was evaporated and the residue suspended in water (5 ml) and extracted with ethyl acetate (2×10 ml). The organic extract was then extracted with 2M hydrochloric acid (2×15 ml). The aqueous layer was basified with 2M sodium hydroxide and extracted with ethyl acetate (2×20 ml), the organic extract was dried over anhydrous magnesium sulphate, filtered and evaporated to yield 6-(2,4-dimethoxyphenyl)-1,4-dimethyl-1,2,3,6-tetrahydropyridine (6) (350 mg, 73%) as a yellow oil, 1H NMR CDCl3 δ?1.55 (s, 3H), 1.9 (m, 1H), 2.2 (s, 3H), 2.5 (m, 2H), 2.95 (m, 1H), 3.8 (s, 6H), 4.1 (m, 1H), 5.2 (m, 1H), 6.5 (m, 2H), 7.3 (d, 1H J=4).

Workup

  1. customAt this time the solvent was evaporated
  2. extractionextracted with ethyl acetate (2×10 ml)
  3. extractionThe organic extract
  4. extractionwas then extracted with 2M hydrochloric acid (2×15 ml)
  5. extractionextracted with ethyl acetate (2×20 ml)
  6. extractionthe organic extract
  7. dry with materialwas dried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-4c172235d32247c69787c42062d864d3
Source dataset
uspto-grants-2009_11
Patent number
US07612101B2

Reaction notes

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