169.
[197]In un provettone Schlenk da 10 mL sono stati introdotti, sotto flusso di N2, 53 mg (0.083
mmoli, 1 equiv.) di 169, 0.44 mL di CH3OH e 13.6 mg di Pd/C al 10%. Impiegando una
pompa a membrana e facendo attenzione ad evitare l’evaporazione tumultuosa del solvente, il provettone è stato sottoposto a tre cicli vuoto-H2. La sospensione è stata mantenuta in
atmosfera di H2 per 18h, sotto energica agitazione magnetica a temperatura ambiente. La
miscela di reazione è stata filtrata su uno strato di celite, lavando il residuo con 2 porzioni di CH3OH. Il solvente dei filtrati riuniti è stato rimosso all’evaporatore rotante e il solido bianco
ottenuto (20 mg) è stato sottoposto a cromatografia flash (SiO2, n-esano:AcOEt = 1:1 →
AcOEt). Dalla separazione cromatografica sono stati recuperati tre frazioni che mostravano, rispettivamente, macchie ad Rf = 0, 0.16 e 0.46. Dopo evaporazione del solvente, la sostanza
meno trattenuta (2.6 mg, Rf = 0.46) ha fornito uno spettro 1H NMR identico a quello del
precursore deamminato 155. Il prodotto intermedio (Rf = 0.16, 3.9 mg) è risultato contenere
principalmente il composto 155, accompagnato da almeno un’altra sostanza in quantità chiaramente visibile ma di difficile identificazione (potrebbe essere il prodotto buono, quello di mono-debenzilazione, …). Infine, le frazioni contenenti i componenti più trattenuti hanno fornito un solido (9.5 mg) che mostrava uno spettro 1H NMR complesso, associabile alla presenza di almeno due componenti principali.
139
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