Tetrahydrofuran → HCID 90370227, compound

HRID 2176026Notes

Reaction equation

HRID 2176026 reaction equation
B.C1COCC1.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]([N:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=O)=[CH:12][CH:11]=1)([O-:9])=[O:8].C1COCC1>CO>[N+:7]([C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][N:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]2)=[CH:14][CH:15]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2723981Borane;tetrahydrofuranHCID 90370154HCID 90370154, compound

Product 1

HCID 90370227HCID 90370227, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A borane-THF complex (1.08 M THF solution) 23 mL was added dropwise to a mixture of 3.02 g of tert-butyl 4-[3-(4-nitrophenyl)propanoyl]piperazine-1-carboxylate and THF 40 mL under ice cooling in an argon atmosphere, followed by stirring for 10 minutes at room temperature, and then heating under reflux was performed for 2 hours. The reaction mixture was cooled with ice, and 30 mL of methanol was added dropwise thereto, followed by stirring for 3 hours at 50° C. The reaction mixture was concentrated under reduced pressure, water and ethyl acetate were added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (5% methanol/chloroform), thereby obtaining 2.78 g of tert-butyl 4-[3-(4-nitrophenyl)propyl]piperazine-1-carboxylate.

Workup

  1. temperatureheating
  2. temperatureunder reflux
  3. waitwas performed for 2 hours
  4. additionwas added dropwise
  5. stirringby stirring for 3 hours at 50° C
  6. concentrationThe reaction mixture was concentrated under reduced pressure, water and ethyl acetate
  7. additionwere added to the residue
  8. extractionfollowed by extraction with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. customthe solvent was removed under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (5% methanol/chloroform)

Sources & evidence

ORD record
ord-801b89d89ded42478fe074c7713d7d61
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

Loading…