Reaktionsgleichung
[CH2:1]([O:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N#N.[CH:19]([CH:21]1[CH2:23][O:22]1)=[CH2:20]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C(#N)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl>[CH2:1]([O:8][N:9]([C@H:21]([CH:19]=[CH2:20])[CH2:23][OH:22])[C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 2.5 °C
Versuchsvorschrift
In a 3 L RBF, a solution of tert-butyl benzyloxycarbamate (Intermediate 153, 86.9 g, 389.22 mmol), N,N(1S,2S)-cyclohexane-1,2-diyl)bis(2-(diphenylphosphino)-1-naphthamide) (18.5 g, 23.39 mmol), Pd2(dba)3-CHCl3 (8.05 g, 7.78 mmol) and TBAB (150.5 g, 466.81 mmol) in acetonitrile (1.8 L) was bubbled with N2 for 30 minutes and the flask was closed with a rubber septum. The solution was then kept in a −20° C. freezer for 2 hrs. 2-vinyloxirane (30 g, 428.02 mmol, 1.10 equiv) was added and the mixture was stirred in the freezer (−20-25° C.) for 3 days. The mixture was filtered and the filtrate was evaporated. The residue was purified by silica gel column eluted with EtOAc/hexane (0-40%) to give the title compound (106 g, 93%) as a pale yellow oil.
Aufarbeitung
- customthe flask was closed with a rubber septum
- filtrationThe mixture was filtered
- customthe filtrate was evaporated
- customThe residue was purified by silica gel column
- washeluted with EtOAc/hexane (0-40%)
Quellen und Nachweise
- ORD-Eintrag
- ord-acb24115ddb249fe8edce1770a1d3d32
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09309245B2
Verknüpfte Notizen
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