Acetic Acid → 2-Methoxy-10-(2-nitroethyl)-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

HRID 2298764Notes

Reaction equation

HRID 2298764 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([CH:15]=[CH:16][N+:17]([O-:19])=[O:18])[C:7]=2[N:20]=1.C(Cl)(Cl)Cl.[BH4-].[Na+].C(O)(=O)C>C(O)(C)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:14]3[C:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)=[C:8]([CH2:15][CH2:16][N+:17]([O-:19])=[O:18])[C:7]=2[N:20]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 694179332-Methoxy-10-[2-nitroethenyl]-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

Product 1

HCID 120351202-Methoxy-10-(2-nitroethyl)-6,7,8,9-tetrahydropyrido[2,3-b]indolizine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Under argon and in an anhydrous medium, 650 mg (2.38 mmol) of the compound obtained in Step D are suspended in 10 ml of isopropanol and 30 ml of chloroform in the presence of 1.5 g of 230-400 mesh silica; 450 mg (11.90 mmol) of sodium borohydride are added slowly. After stirring for 30 minutes at room temperature, acetic acid is added and the reaction mixture is filtered over a glass frit. After removal of the solvents by evaporation, the residue is diluted in dichloromethane and washed with water. The organic phase is then dried over magnesium sulphate, filtered and concentrated to yield the title compound in the form of a yellow solid.

Workup

  1. filtrationthe reaction mixture is filtered over a glass frit
  2. customAfter removal of the solvents
  3. customby evaporation
  4. additionthe residue is diluted in dichloromethane
  5. washwashed with water
  6. dry with materialThe organic phase is then dried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f14bfbcb44db4787b9a52515b5d48798
Source dataset
uspto-grants-2002_12
Patent number
US06495543B1

Reaction notes

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