Acetic Acid → HCID 71278653, compound

HRID 1749861Notes

Reaction equation

HRID 1749861 reaction equation
[C:1]([C:4]1[C:12]2[O:11][CH2:10][C:9](=[O:13])[C:8]=2[CH:7]=[CH:6][C:5]=1[OH:14])(=O)[CH3:2].C(O)(=O)C.[C:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:14][C:5]1[CH:6]=[CH:7][C:8]2[C:9](=[O:13])[CH2:10][O:11][C:12]=2[C:4]=1[CH:1]([N:29]1[CH2:28][CH2:27][N:26]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:31][CH2:30]1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86682017HCID 86682017, compound

Product 1

HCID 71278653HCID 71278653, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-acetyl-6-hydroxybenzofuran-3(2H)-one (0.60 g, 3.1 mmol) in methylene chloride (25 mL) was added with acetic acid (0.25 mL) and N-Boc-piperazine (0.64 g, 3.4 mmol), and the mixture was stirred at room temperature for 10 minutes. The reaction mixture was cooled to 0° C., and then added portionwise with sodium triacetoxyborohydride (0.84 g, 4.1 mmol). After completion of the addition, the ice bath was removed to allow the reaction mixture to warm to room temperature, and the mixture was stirred at the same temperature for 20 hours. The reaction mixture was extracted with methylene chloride, and then the organic layer was successively washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (100:0→97:3)) to obtain tert-butyl 4-[1-(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)ethyl]piperazine-1-carboxylate (0.74 g, 90%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. additionAfter completion of the addition
  3. customthe ice bath was removed
  4. temperatureto warm to room temperature
  5. stirringthe mixture was stirred at the same temperature for 20 hours
  6. extractionThe reaction mixture was extracted with methylene chloride
  7. washthe organic layer was successively washed with water, saturated aqueous sodium hydrogencarbonate, and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (100:0→97:3))

Sources & evidence

ORD record
ord-3d2edec66f194372a063f8d459926f83
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

Loading…