Reaktion #77157

Reaktionsgleichung

[N,N′-di(tert-butoxycarbonyl)]3-(benzyloxycarbonylamino)-1-propoxyguanidine

→

title compound

Ausbeute 28.3%

[N,N′-Di(tert-butoxycarbonyl)]3-amino-1-propoxyguanidine

Ausbeute 28.3%

Lösungsmittel

ethanol

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe catalyst was removed by filtration through Celite
2. 2
   Einengenthe filtrate was concentrated in vacuo
3. 3
   Sonstigethe residue was purified by Waters Sep-Pak (10 g, 95:5 methylene chloride:methanol saturated with amnonia)

Vorschrift

A mixture of [N,N′-di(tert-butoxycarbonyl)]3-(benzyloxycarbonylamino)-1-propoxyguanidine (760 mg, 1.7 mmol), as prepared in the preceding step, and 10% Pd/C (80 mg) in ethanol (20 mL) and tetrahydrofuran (20 mL) was hydrogenated under hydrogen (balloon) for 30 min. The catalyst was removed by filtration through Celite, the filtrate was concentrated in vacuo, and the residue was purified by Waters Sep-Pak (10 g, 95:5 methylene chloride:methanol saturated with amnonia) to give the title compound as a colorless oil (160 mg,28%). 1H-NMR (300 MHz, CDCl3) δ4.12 (t, J=6.1 Hz, 2H), 2.85 (t, J=6.7 Hz, 2H), 1.84 (pentet, J=6.2 Hz, 2H), 1.50 (s, 9H), 1.48 (s, 9H).

Quelle