Ammonium Chloride → HCID 66696998, compound

HRID 1500142Notes

Reaction equation

HRID 1500142 reaction equation
[CH2:1]([C:3]1[CH2:4][CH:5]2[CH:8]([CH:9]=1)[C:7]([CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])([CH2:10][N+:11]([O-])=O)[CH2:6]2)[CH3:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:11][CH2:10][C:7]1([CH2:14][C:15]([OH:17])=[O:16])[CH2:6][CH:5]2[CH:8]1[CH:9]=[C:3]([CH2:1][CH3:2])[CH2:4]2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 66803796HCID 66803796, compound

Product 1

HCID 66696998HCID 66696998, compoundYield 43.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Tert-butyl [3-ethyl-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (1.09 g, 4.71 mmol) was dissolved in ethanol (10 mL) and water (5 mL). To the solution, iron powder (1.32 g, 23.5 mmol) and ammonium chloride (249.6 mg, 4.71 mmol) were added, and the mixture was stirred for 2 hours under heating to reflux. The mixture was allowed to cool, then diluted with saturated saline, a saturated aqueous solution of sodium bicarbonate, and ethyl acetate, and filtered through Celite to remove insoluble matter. The filtrate was separated into organic and aqueous layers. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure. To the residue, a 4 N solution of hydrochloric acid in ethyl acetate (20 mL) was added, and the mixture was stirred at room temperature for 1 hour. Then, the solvent was distilled off under reduced pressure. The residue was suspended in dichloromethane. To the suspension, triethylamine was added dropwise, and the resulting powder was collected by filtration, then washed with dichloromethane, and then dried to obtain the compound of interest as a white powder (425.1 mg, 43%).

Workup

  1. temperatureunder heating to reflux
  2. temperatureto cool
  3. additiondiluted with saturated saline
  4. filtrationa saturated aqueous solution of sodium bicarbonate, and ethyl acetate, and filtered through Celite
  5. customto remove insoluble matter
  6. customThe filtrate was separated into organic and aqueous layers
  7. washThe organic layer was washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was then distilled off under reduced pressure
  10. additionTo the residue, a 4 N solution of hydrochloric acid in ethyl acetate (20 mL) was added
  11. stirringthe mixture was stirred at room temperature for 1 hour
  12. distillationThen, the solvent was distilled off under reduced pressure
  13. additionTo the suspension, triethylamine was added dropwise
  14. filtrationthe resulting powder was collected by filtration
  15. washwashed with dichloromethane
  16. customdried

Sources & evidence

ORD record
ord-ee21a949a76f4f8493109742812d9c87
Source dataset
uspto-grants-2015_12
Patent number
US09206104B2

Reaction notes

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