Water → (3S,6R)-3-aminohexahydro-6-tert-butyldimethylsilyloxy-2H-azepin-2-one
Reaktionsgleichung
C(OC([NH:8][C@H:9]1[CH2:15][CH2:14][C@@H:13]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:12][NH:11][C:10]1=[O:24])=O)(C)(C)C.C[Si](I)(C)C.O>C(Cl)Cl.CO>[NH2:8][C@H:9]1[CH2:15][CH2:14][C@@H:13]([O:16][Si:17]([C:20]([CH3:22])([CH3:21])[CH3:23])([CH3:18])[CH3:19])[CH2:12][NH:11][C:10]1=[O:24]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
(3S,6R)-3-(tert-butoxycarbonyl)aminohexahydro-6-tert-butyldimethylsilyloxy-2H-azepin-2-one (8.0 g, 22 mmol) is dissolved in 40 mL of CH2Cl2 and cooled to −78° C. Trimethylsilyl iodide (3.5 mL, 24.5 mmol) is added slowly. The mixture is allowed to react at −78° C. for 30 min. The reaction is warmed to 0° C. and stirred for 15 min. The solution turned yellow. The reaction is quenched with NH4HCO3 (3.43 g, 44 mmol) dissolved in 30 mL of CH3OH, and 15 mL water. The mixture is concentrated and chromatographed with a 95:5 mixture of CH2Cl2 and methanol to yield 5.45 g (96%) of (3S,6R)-3-aminohexahydro-6-tert-butyldimethylsilyloxy-2H-azepin-2-one as a white solid: 1H NMR (CDCl3) δ 5.61 (s, 1H), 3.88 (s, 1H), 3.42 (d, J=8 Hz, 1H), 3.32(dd, J=6 Hz and 16 Hz, 1H), 3.06 (m, 1H), 1.87 (m, 2H), 1.76 (m, 1H), 1.65 (s, 3H), 0.83 (s, 9H), 0.001 (s, 6H).
Aufarbeitung
- customto react at −78° C. for 30 min
- temperatureThe reaction is warmed to 0° C.
- concentrationThe mixture is concentrated
- customchromatographed with a 95:5 mixture of CH2Cl2 and methanol
Quellen und Nachweise
- ORD-Eintrag
- ord-a4a256f6a2b2401d97057b2545391dfe
- Quelldatensatz
- uspto-grants-2003_07
- Patentnummer
- US06599898B2
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