Pyrrolidine → HCID 89807213, compound

HRID 1526355Notes

Reaction equation

HRID 1526355 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][N:9]=1)[CH:5]=O.[NH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][N:9]=1

Participants

6

Reactant 4

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 27629912-Bromo-4-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 89807213HCID 89807213, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-bromoisonicotinaldehyde (400 mg) and pyrrolidine (0.197 mL) in acetonitrile (16 mL) was added sodium triacetoxyborohydride (547 mg) at room temperature, and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (445 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-005d559c976f4f20b86cfd430e4db207
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

Loading…