Ammonium Chloride → HCID 131728909, compound

HRID 551659Notes

Reaction equation

HRID 551659 reaction equation
[N+:1]([CH2:4][C@@:5]1([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:11][C@H:10]2[C@@H:6]1[CH:7]=[C:8]([CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9]2)([O-])=O.[Cl-].[NH4+]>C(O)C.[Fe]>[NH2:1][CH2:4][C@@:5]1([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:11][C@H:10]2[C@@H:6]1[CH:7]=[C:8]([CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[CH2:9]2

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 131728908HCID 131728908, compound

Product 1

HCID 131728909HCID 131728909, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Tert-butyl(±)-[(1S,5R,6R)-6-(nitromethyl)-3-cyclopentylbicyclo[3.2.0]hept-3-en-6-yl]acetate (3.30 g, 9.8 mmol) was dissolved in ethanol (60 mL). To the solution, iron powder (4.47 g, 80.0 mmol) and then an aqueous ammonium chloride (0.54 g, 10.0 mmol) solution (20 mL) were added, and the mixture was stirred for 4.5 hours under heating to reflux. The mixture was allowed to cool and then filtered through Celite to remove insoluble matter. The solution was concentrated, and the residue was diluted with ethyl acetate. The dilution was washed with a saturated aqueous solution of sodium bicarbonate and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the compound of interest as a colorless oil substance (2.00 g, 67%).

Workup

  1. temperatureunder heating to reflux
  2. temperatureto cool
  3. filtrationfiltered through Celite
  4. customto remove insoluble matter
  5. concentrationThe solution was concentrated
  6. additionthe residue was diluted with ethyl acetate
  7. washThe dilution was washed with a saturated aqueous solution of sodium bicarbonate
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThen, the solvent was distilled off under reduced pressure
  10. customthe residue was purified by silica gel column chromatography
  11. customto obtain the compound of interest as a colorless oil substance (2.00 g, 67%)

Sources & evidence

ORD record
ord-b2e2225cdb8e412b9b5c3e2b4cca3ec2
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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