Ammonium Chloride → Tert-butyl[(1s,5r,6r)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

HRID 551611Notes

Reaction equation

HRID 551611 reaction equation
[N+:1]([CH2:4][C@@:5]1([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][C@H:10]2[C@@H:6]1[CH:7]=[CH:8][CH2:9]2)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:1][CH2:4][C@@:5]1([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][C@H:10]2[C@@H:6]1[CH:7]=[CH:8][CH2:9]2

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 91600480Tert-butyl[(1s,5r,6r)-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

Product 1

HCID 66803936Tert-butyl[(1s,5r,6r)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Tert-butyl(±)-[(1S,5R,6R)-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (1.98 g, 7.41 mmol) was dissolved in ethanol (20 mL) and water (10 mL). To the solution, iron powder (2.07 g, 37.0 mmol) and ammonium chloride (392.7 mg, 7.41 mmol) were added, and the mixture was stirred for 4.5 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 and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain the compound of interest as a pale yellow solid (1.99 g, this compound was used directly in the next reaction without being purified).

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. distillationThen, the solvent was distilled off under reduced pressure
  10. customto obtain the compound of interest as a pale yellow solid (1.99 g
  11. customthis compound was used directly in the next reaction
  12. customwithout being purified)

Sources & evidence

ORD record
ord-6830105d85cc401ba75640cdd395c9ff
Source dataset
uspto-grants-2011_05
Patent number
US07947738B2

Reaction notes

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