Reaktion #638796

Reaktionsgleichung

tert-butyl[(1R,5S,6S)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate

→

powder

(−)-[(1R,5S,6S)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetic acid

Lösungsmittel

hydrochloric acid ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure
2. 2
   workup.ADDITIONTo the suspension, triethylamine was added dropwise
3. 3
   Filtrationthe resulting powder was collected by filtration
4. 4
   Waschenwashed with dichloromethane
5. 5
   Sonstigedried
6. 6
   Sonstigeto obtain a white powder A (6.85 g)
7. 7
   workup.DISTILLATIONFrom the filtrate, the solvent was distilled off under reduced pressure
8. 8
   workup.ADDITIONTo the residue, a 4 N hydrochloric acid-ethyl acetate solution (200 mL) was then added again
9. 9
   workup.STIRRINGthe mixture was stirred at room temperature for 2 hours
10. 10
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
11. 11
    workup.ADDITIONTo the residue, triethylamine was added dropwise
12. 12
    Filtrationthe resulting powder was collected by filtration
13. 13
    Waschenwashed with dichloromethane
14. 14
    Sonstigedried
15. 15
    Sonstigeto obtain a white powder B (2.48 g)
16. 16
    Waschenwashed with ethanol and ethyl acetate

Vorschrift

A 4 N hydrochloric acid-ethyl acetate solution (200 mL) was added to tert-butyl[(1R,5S,6S)-6-(aminomethyl)bicyclo[3.2.0]hept-3-en-6-yl]acetate (17.53 g, 7.4 mmol), and the mixture was stirred at room temperature for 1.5 hours. 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 a white powder A (6.85 g). From the filtrate, the solvent was distilled off under reduced pressure. To the residue, a 4 N hydrochloric acid-ethyl acetate solution (200 mL) was then added again, and the mixture was stirred at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and the residue was suspended in dichloromethane. To the residue, triethylamine was added dropwise, and the resulting powder was collected by filtration, then washed with dichloromethane, and then dried to obtain a white powder B (2.48 g). This white powder B was combined with the above-obtained white powder A and washed with ethanol and ethyl acetate to obtain the compound of interest as a white powder (7.39 g, 55%).

Quelle