Benzyl trans(+/-)-4-[(tert-butoxycarbonyl)amino]-3-{[tert-butyl(dimethyl)silyl]oxy}piperidine-1-carboxylate → tert-Butyl (trans(+/-)-3-{[tert-butyl(dimethyl)silyl]oxy}piperidin-4-yl)carbamate
Reaktionsgleichung
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12](C(OCC2C=CC=CC=2)=O)[CH2:11][C@H:10]1[O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[Si:26]([O:25][C@H:10]1[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][CH2:13][NH:12][CH2:11]1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of (+/−)-(3R,4R)-benzyl 4-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate (13 g, 28.0 mmol) and Pd/C (5% on carbon, 1.786 g, 0.839 mmol) in methanol (250 mL) was hydrogenated at 30 psi overnight. The mixture was filtered through Celite and the filtrate was concentrated in vacuo and further dried under high vacuum at 40° C. overnight. The crude product was used without purification. (+/−)-tert-butyl ((3R,4R)-3-((tert-butyldimethylsilyl)oxy)piperidin-4-yl)carbamate (8.8 g, 26.6 mmol, 95% yield) was obtained as a white solid.
Aufarbeitung
- customwas hydrogenated at 30 psi overnight
- filtrationThe mixture was filtered through Celite
- concentrationthe filtrate was concentrated in vacuo
- customfurther dried under high vacuum at 40° C. overnight
- customThe crude product was used without purification
Quellen und Nachweise
- ORD-Eintrag
- ord-c235ee6d722841838ed611ea6b6fe686
- Quelldatensatz
- uspto-grants-2015_01
- Patentnummer
- US08940736B2
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