Methanol → HCID 86694324, compound

HRID 69121Notes

Reaction equation

HRID 69121 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=O)[CH:2]=1.B.O1CCCC1.CO>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][N:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH2:16]2)[CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 15289252HCID 15289252, compound

Product 1

HCID 86694324HCID 86694324, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, to a solution of 1.5 g of tert-butyl 4-[3-(pyridin-3-yl)propanoyl]piperazine-1-carboxylate in 25 mL of tetrahydrofuran was added 7 mL of a 1 M borane/tetrahydrofuran solution under ice-cooling. The mixture was heated to reflux for 6 hours, and then cooled to room temperature, and 10 mL of methanol was added thereto, followed by further heating to reflux for 16 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure, and a mixture of a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate was added thereto. The aqueous layer was separated, and then the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 1.43 g of tert-butyl 4-[3-(pyridin-3-yl)propyl]piperazine-1-carboxylate.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 6 hours
  4. temperatureby further heating
  5. temperatureto reflux for 16 hours
  6. temperatureAfter cooling to room temperature
  7. concentrationthe mixture was concentrated under reduced pressure
  8. additiona mixture of a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
  9. additionwas added
  10. customThe aqueous layer was separated
  11. washthe organic layer was washed with saturated brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customThe solvent was evaporated under reduced pressure
  14. customthe residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-2da19d95010a42a18b7dd1c4d4a5406b
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

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