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

HRID 324620Notes

Reaction equation

HRID 324620 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 52.97g, 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-be745bf2fffa4e06815aa7b3452f80bb
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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