Triethylamine → HCID 22004806, compound

HRID 1636622Notes

Reaction equation

HRID 1636622 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH2:12][C:13]([CH3:15])=[CH2:14])[C:10]=1[OH:11])[CH:7]([CH2:16][CH2:17][NH:18][C:19](=[O:22])[CH2:20][CH3:21])[CH2:6][CH2:5]2.C(N(CC)CC)C.S([O-])([O-])(=[O:32])=S.[Na+].[Na+]>ClCCl>[Br:1][C:2]1[C:10]2[O:11][C:13]([CH2:15][OH:32])([CH3:14])[CH2:12][C:9]=2[C:8]2[CH:7]([CH2:16][CH2:17][NH:18][C:19](=[O:22])[CH2:20][CH3:21])[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24477Sodium ThiosulfateHCID 10883054HCID 10883054, compound

Product 1

HCID 22004806HCID 22004806, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[2-(5-bromo-6-hydroxy-7-(2-methyl-2-propenyl)indan-1-yl)ethyl]propionamide (550 mg, 1.5 mmol.) in dichloromethane (5 mL) was cooled with ice. To the solution were added triethylamine (0.2 mL, 1.5 mmol.) and methachloroperbenzoic acid (1.0 g, 4.1 mmol.). The mixture was stirred for two hours at room temperature. The reaction mixture was poured into an aqueous solution of sodium thiosulfate. The organic matter was extracted with ethyl acetate. The extract solution was washed with 1N HCl and a saturated aqueous solution of sodium hydrogencarbonate, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residue was dissolved in dichloromethane, to which was added triethylamine (1 mL). The mixture was stirred for 2 hours at room temperature. The solvent was distilled off under reduced pressure, and the residue was purified by means of silica gel column chromatography (chloroform:methanol=10:1) to afford the title compound (yield 420 mg, 73%) as an oily product.

Workup

  1. extractionThe organic matter was extracted with ethyl acetate
  2. washThe extract solution was washed with 1N HCl
  3. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, which was then dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent
  5. dissolutionThe residue was dissolved in dichloromethane, to which
  6. additionwas added triethylamine (1 mL)
  7. stirringThe mixture was stirred for 2 hours at room temperature
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by means of silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-ab41526d56864d30975c914d9961d3da
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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