Reaktion #60330

Reaktionsgleichung

4-Azido-7-cyanochroman

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title compound

4-amino-7-cyanochroman

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepurged with N2
2. 2
   workup.ADDITIONPd/C (10%, 0.6 g) was added
3. 3
   Sonstigethe reaction was purged with N2
4. 4
   SonstigeThe reaction was purged with H2
5. 5
   Sonstigewas complete by TLC analysis (approximately 1 h)
6. 6
   SonstigeThe reaction was purged with N2
7. 7
   Filtrationfiltered through Celite®
8. 8
   WaschenThe Celite®was washed with MeOH
9. 9
   EinengenThe solution was concentrated in vacuo
10. 10
    Sonstigeto provide a residue which
11. 11
    Sonstigewas purified by column chromatography (silica, 3% MeOH in CH2Cl2 plus 0.5% NH4OH)

Vorschrift

4-Azido-7-cyanochroman (Step D) (4.3 g, 21 mmol) was dissolved in EtOAc (200 mL) and purged with N2. Pd/C (10%, 0.6 g) was added and the reaction was purged with N2. The reaction was purged with H2 and rapidly stirred under a H2 atmosphere until consumption of starting material was complete by TLC analysis (approximately 1 h). The reaction was purged with N2, and filtered through Celite®. The Celite®was washed with MeOH. The solution was concentrated in vacuo to provide a residue which was purified by column chromatography (silica, 3% MeOH in CH2Cl2 plus 0.5% NH4OH) to provide the title compound. TLC Rf=0.3 (5% MeOH in CH2Cl2 plus 0.5% Et3N.

Quelle