Boron tribromide → N-[2-[(1S)-5-Bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamide

HRID 324619Notes

Reaction equation

HRID 324619 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11]C)[C@H:7]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH2:6][CH2:5]2.B(Br)(Br)Br>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[OH:11])[C@H:7]([CH2:13][CH2:14][NH:15][C:16](=[O:19])[CH2:17][CH3:18])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 11012817HCID 11012817, compound

Product 1

HCID 11066924N-[2-[(1S)-5-Bromo-2,3-dihydro-6-hydroxy-1H-inden-1-yl]ethyl]propanamideYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-N-[2-(5-bromo-6-methoxyindan-1-yl)ethyl]propionamide (56.7 g, 174 mmol.) in dichloromethane (400 mL) was cooled to −30° C. To the solution was added dropwise slowly boron tribromide (95.8 g, 382 mmol.). The reaction mixture was stirred for 30 minutes while keeping at temperatures ranging from −20 to −15° C. The reaction mixture was poured into ice-water, which was stirred for further 10 minutes at room temperature. The organic matter was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, 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) to afford the title compound (yield 51.12 g, 94%).

Workup

  1. customranging from −20 to −15° C
  2. stirringwas stirred for further 10 minutes at room temperature
  3. extractionThe organic matter was extracted with ethyl acetate
  4. washThe extract solution was washed with a saturated aqueous saline solution and water, which
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe residue was purified by means of silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-bcbbeee576b149d28013ab89cab31c49
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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