Ammonium Chloride → HCID 67196703, compound

Tert-butyl(±)-[(1S,5R,6R)-3-allyl-6-(nitromethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (335.2 mg, 1.09 mmol) was dissolved in ethanol (10 mL) and water (5 mL). To the solution, iron powder (611.0 mg, 10.9 mmol) and ammonium chloride (57.8 mg, 1.09 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 hydrochloric acid-ethyl acetate solution (10 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 (68.5 mg, 28%).

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 hydrochloric acid-ethyl acetate solution (10 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

ORD record

ord-2dc324742fc644628328462458b487f7

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2