Ammonium Chloride → HCID 59509754, compound

HRID 551695Notes

Reaction equation

HRID 551695 reaction equation
[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@:8]1([CH2:17][N+:18]([O-])=O)[CH2:14][C@@H:13]2[C@H:9]1[CH:10]=[C:11]([CH2:15][CH3:16])[CH2:12]2)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[C:1]([O:5][C:6](=[O:21])[CH2:7][C@@:8]1([CH2:17][NH2:18])[CH2:14][C@@H:13]2[C@H:9]1[CH:10]=[C:11]([CH2:15][CH3:16])[CH2:12]2)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 91092873HCID 91092873, compound

Product 1

HCID 59509754HCID 59509754, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Tert-butyl[(1R,5S,6S)-3-ethyl-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (7.0 g, 23.7 mmol) was dissolved in ethanol (60 mL) and water (21 mL). To the solution, iron powder (13.27 g, 237 mmol) and ammonium chloride (628.1 mg, 11.9 mmol) were added, and the mixture was stirred for 5.5 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. The organic layer was dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain the compound of interest as a pale yellow oil substance (7.02 g, <100%).

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 materialThe organic layer was dried over anhydrous magnesium sulfate
  9. distillationThen, the solvent was distilled off under reduced pressure
  10. customto obtain the compound of interest as a pale yellow oil substance (7.02 g, <100%)

Sources & evidence

ORD record
ord-8b1004754ba44bde8de5e63b5b8ea0f2
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

Loading…