Hydrochloric Acid → N-[2-[(1S)-5-Bromo-2,3-dihydro-6-(2-propen-1-yloxy)-1H-inden-1-yl]ethyl]propanamide

HRID 1636593Notes

Reaction equation

HRID 1636593 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C@H:7]([CH2:12][CH2:13][NH:14][C:15](=[O:18])[CH2:16][CH3:17])[CH2:6][CH2:5]2.[H-].[Na+].[CH2:21](Br)[CH:22]=[CH2:23].Cl>CN(C)C=O>[CH2:23]([O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C@H:7]2[CH2:12][CH2:13][NH:14][C:15](=[O:18])[CH2:16][CH3:17])=[CH:3][C:2]=1[Br:1])[CH:22]=[CH2:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 11066924N-[2-[(1S)-5-Bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide

Product 1

HCID 10871865N-[2-[(1S)-5-Bromo-2,3-dihydro-6-(2-propen-1-yloxy)-1H-inden-1-yl]ethyl]propanamideYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-N-[2-(5-bromo-6-hydroxyindan-1-yl)ethyl]propionamide (48.8 g, 156 mmol.) in N,N-dimethylformamide (110 mL) was cooled with ice, to which was gradually added sodium hydride (6.35 g, 172 mmol., content 65%). The mixture was stirred for about 15 minutes. When the bubbling of hydrogen gas ceased, allyl bromide (22.7 g, 188 mmol.) was added, and the mixture was stirred for 30 minutes under ice-cooling. The reaction mixture was poured into ice-water, which was neutralized with dilute hydrochloric acid. The organic matter was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel gel column chromatography (ethyl acetate) to afford the title compound (yield 52.97 g, 96%).

Workup

  1. customWhen the bubbling of hydrogen gas
  2. stirringthe mixture was stirred for 30 minutes under ice-
  3. temperaturecooling
  4. extractionThe organic matter was extracted with ethyl acetate
  5. washThe extract solution was washed with a saturated aqueous saline solution and water, which
  6. dry with materialwas then dried over magnesium sulfate
  7. distillationby distilling off the solvent under reduced pressure
  8. customThe residue was purified by means of silica gel gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-fe1f99efe303455ebfb30240dd4b4cf4
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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