6-allyl-3-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-yl)-6-phenyl-1,3-oxazinan-2-one → 6-allyl-3-((S)-3-hydroxy-3-methylbutan-2-yl)-6-phenyl-1,3-oxazinan-2-one
Reaktionsgleichung
[CH2:1]([C:4]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]([O:16][Si](C(C)(C)C)(C)C)([CH3:15])[CH3:14])[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:1]([C:4]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]([OH:16])([CH3:14])[CH3:15])[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A mixture of 6-allyl-3-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-yl)-6-phenyl-1,3-oxazinan-2-one isomer 1 (80 mg, 0.19 mmol) in 20% TFA/DCM (2 mL) was stirred for 30 min at 0° C. The mixture was concentrated to give crude 6-allyl-3-((S)-3-hydroxy-3-methylbutan-2-yl)-6-phenyl-1,3-oxazinan-2-one isomer 1 (50 mg, 86%). LC-MS Method 2 tR=1.85 min, m/z=326, 304; 1H NMR (CDCl3) 1.07 (m, 6H), 1.18 (s, 3H), 2.15 (m, 1H), 2.25 (m, 1H), 2.58 (m, 2H), 2.90 (m, 1H), 3.08 (m, 1H), 3.20 (m, 1H), 5.02 (m, 2H), 5.68 (m, 1H), 7.22 (3H), 7.31 (2H).
Aufarbeitung
- concentrationThe mixture was concentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-61b659c3b56e49f2b3b5cf67577ef631
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08748444B2
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