Reaktionsgleichung
CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=[C:15]([O:22]C)C=C4)N(CC2)C1.[C:59]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])(=[O:65])CCCC=C.CCOC(C)=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].O.[CH2:87]([OH:91])[CH2:88][CH2:89][CH3:90]>>[OH:91][C@H:87]([CH2:15][OH:22])[CH2:88][CH2:89][CH2:90][C:59]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65]Komponenten
6
Edukt 5
Produkt 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a suspension of AD-mix-α (70 g) in water/butanol 1:1 (512 mL) cooled to 0° C., tert-butyl hex-5-enoate (8.5 g, 49.92 mmol) was added. The reaction mixture was stirred at 4° C. for 70 hrs. Then the reaction mixture was cooled to 0° C. and EtOAc (280 mL), followed by continuous portionwise addition of sodium metabisulfite (20.6 g). The mixture was stirred for 30 min at 0° C. and at rt for 1 hour. The organic layer was separated and the aqueous phase extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. Chromatography over silica gel eluting with EtOAc 100% afforded the title compound as a pale yellow oil.
Aufarbeitung
- temperatureThen the reaction mixture was cooled to 0° C.
- stirringThe mixture was stirred for 30 min at 0° C. and at rt for 1 hour
- customThe organic layer was separated
- extractionthe aqueous phase extracted with ethyl acetate
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-13b28ff0e5b845a0bd86d1e91e31ebc1
- Quelldatensatz
- uspto-grants-2012_02
- Patentnummer
- US08119806B2
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