1-Benzyl-cis-3-t-butoxycarbonylamino-4-methylpyrrolidine → (3S,4S)-3-(Boc-amino)-4-methylpyrrolidine
Reaktionsgleichung
C1(C[N:8]2[CH2:12][C@H:11]([CH3:13])[C@H:10]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9]2)C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:20][C:18]([CH3:21])([O:17][C:15]([NH:14][C@H:10]1[C@@H:11]([CH3:13])[CH2:12][NH:8][CH2:9]1)=[O:16])[CH3:19]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of 1.5 g(5.2 mmol) of cis-1-phenylmethyl-3-(1,1-dimethylethoxycarbonylamino)-4-methylpyrrolidine (cf. U.S. Pat. No. 4,753,953) in 50 mL methanol was treated with 200 mg of Pd(OH)2 /C followed by hydrogenation under 1 atmosphere of H2 for 3.5 h. The mixture was filtered through celite, washing the filter cake with methanol. The filtrate was concentrated in vacuo to afford a colorless oil, which was used directly in the next step. 1H NMR (CD3OD) δ 4.85, 4.03, 3.14, 3.05, 2.66, 2.45, 2.23, 1.46, 0.95.