Water → 5-Methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridine

HRID 518800Notes

Reaction equation

HRID 518800 reaction equation
[BH4-].[Na+].[I-].[CH3:4][O:5][C:6]1[CH:7]=[N+:8]([CH3:25])[CH:9]=[CH:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([O:21][CH:22]([CH3:24])[CH3:23])[CH:13]=1.O.C(OCC)(=O)C>C(O)C>[CH3:4][O:5][C:6]1[CH2:7][N:8]([CH3:25])[CH2:9][CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([O:21][CH:22]([CH3:24])[CH3:23])[CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 866979693-Methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide

Product 1

HCID 866979715-Methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridineYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

672 mg of NaBH4 are added, in portions, to a suspension of 5.09 g of 3-methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]pyridinium iodide in 90 ml of ethanol brought to 5° C. the reaction medium is stirred for 30 minutes at ambient temperature. 50 ml of water and 100 ml of ethyl acetate are added. The two phases are separated, and the aqueous phase is washed with twice 50 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. Purification is carried out by flash chromatography on silica gel (40-63 μm), elution being carried out with a mixture of dichloromethane and acetone (95/5 to 80/20). 2.78 g of 5-methoxy-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]-1,2,3,6-tetrahydropyridine are obtained in the form of a brown oil.

Workup

  1. custombrought to 5° C.
  2. customThe two phases are separated
  3. washthe aqueous phase is washed with twice 50 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification
  8. washis carried out by flash chromatography on silica gel (40-63 μm), elution
  9. additionbeing carried out with a mixture of dichloromethane and acetone (95/5 to 80/20)

Sources & evidence

ORD record
ord-4addf5e4ac614f7baa910f06935a035b
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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