Reaktionsgleichung
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[CH2:20][C:21]([OH:23])=O)=[C:8]2[CH3:25])=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(Cl)(=O)C(C)(C)C.[CH:45]([C@@H:48]1[CH2:52][O:51][C:50](=[O:53])[NH:49]1)([CH3:47])[CH3:46].[Li]CCCC>C1COCC1>[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH2:18][CH:19]([CH3:24])[CH2:20][C:21]([N:49]3[C@H:48]([CH:45]([CH3:47])[CH3:46])[CH2:52][O:51][C:50]3=[O:53])=[O:23])=[C:8]2[CH3:25])=[CH:4][CH:3]=1Komponenten
7
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
To a solution of acid from Step 6 (1.0 g, 2.3 mmol) in THF (20 mL) at 0° C. was added KHMDS (0.64M/toluene, 4.0 mL, 2.6 mmol) followed by pivaloyl chloride (0.31 mL, 2.6 mmol). After 30 rain at 0° C., the solution was cooled to -78° C., and a cloudy solution of (R)-4-isopropyl oxazolidinone (0.35 g, 2.7 mmol) and BuLi (1.6M/hexane, 1.7 mL, 2.7 mmol) in THF (20 mL) was added via double-tipped needle. After 10 min at -78° C., the reaction was warmed to 0° C. for 1 h, at which point it was quenched by the addition of saturated NH4Cl solution. Following EtOAc/H2O work-up, the two diastereomers were obtained by flash chromatography (1:5 EtOAc/hexane). isomer A=0.55 g, isomer B =0.52 g.
Aufarbeitung
- temperaturethe reaction was warmed to 0° C. for 1 h, at which point it
- customwas quenched by the addition of saturated NH4Cl solution
- customFollowing EtOAc/H2O work-up, the two diastereomers were obtained by flash chromatography (1:5 EtOAc/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-778a698ec00c47aa8720b77ff6514c91
- Quelldatensatz
- uspto-grants-1997_06
- Patentnummer
- US05639780
Verknüpfte Notizen
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