Bromine → HCID 58435488, compound

HRID 1627058Notes

Reaction equation

HRID 1627058 reaction equation
[Br:1]Br.[CH2:3]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]3[CH2:11][CH2:12][C@@H:13]([CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])[C:14]=3[C:4]1=2.C([O-])(=O)C.[Na+]>CO>[Br:1][C:8]1[C:5]2[O:6][CH2:7][CH2:3][C:4]=2[C:14]2[C@H:13]([CH2:15][CH2:16][NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH2:12][CH2:11][C:10]=2[CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 208902RamelteonHCID 517045Sodium Acetate

Product 1

HCID 58435488HCID 58435488, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Bromine was added dropwise into a solution of (S)—N-(2-[1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl]ethyl)propionamide (27.4 g, 0.11 mol) and sodium acetate (10.4 g, 0.13 mol) in methanol (200 mL) with ice-cooling. The mixture was allowed to stir for 1.5 hours with ice-cooling, which was quenched with sodium hydrogen sulfite and poured into water, followed by extracting with ethyl acetate. The extracted solution was washed with water and a saturated aqueous solution of sodium hydrogencarbonate, which was dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate:hexane=8:2) to afford the title compound (yield 33.1 g, 93%) as a white powder.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customwhich was quenched with sodium hydrogen sulfite
  4. additionpoured into water
  5. extractionby extracting with ethyl acetate
  6. washThe extracted solution was washed with water
  7. dry with materiala saturated aqueous solution of sodium hydrogencarbonate, which was dried over anhydrous magnesium sulfate
  8. distillationby distilling off the solvent under reduced pressure
  9. customThe residue was purified by means of silica gel column chromatography (ethyl acetate:hexane=8:2)

Sources & evidence

ORD record
ord-805846f194044a6fb97a19f5c0231fea
Source dataset
uspto-grants-2014_07
Patent number
US08785491B2

Reaction notes

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