1,4-Bis(dihydroquinidine)phthalazine → (2R)-2-(3-bromophenyl)-1,2-propanediol
Reaktionsgleichung
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH:9]=C)[CH:3]=1.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:25]([O:32]C)C=C4)N(CC2)C1.C([OH:73])(C)(C)C.O>>[Br:1][C:2]1[CH:3]=[C:4]([C@:8]([OH:73])([CH3:9])[CH2:25][OH:32])[CH:5]=[CH:6][CH:7]=1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 4 °C
Versuchsvorschrift
A mixture of 1-bromo-3-(2-propenyl)benzene from step 1 (2.9 g, 15 mmol) and AD-mix-β (Aldrich, 21.0 g) in t-BuOH-H2O (1:1, 150 mL) was vigorously stirred at 4° C. for 16 h. The reaction was quenched with solid Na2SO3 (5.0 g) and diluted with ethyl acetate (150 mL). The aqueous was separated and extracted with ethyl acetate. The combine organic phase was washed with brine, dried and filtered through a short path of silica gel. Removal of the solvent gave essentially pure title compound.
Aufarbeitung
- customThe reaction was quenched with solid Na2SO3 (5.0 g)
- additiondiluted with ethyl acetate (150 mL)
- customThe aqueous was separated
- extractionextracted with ethyl acetate
- washThe combine organic phase was washed with brine
- customdried
- filtrationfiltered through a short path of silica gel
- customRemoval of the solvent
Quellen und Nachweise
- ORD-Eintrag
- ord-086a6a894d3a430c80f8e471244168a9
- Quelldatensatz
- uspto-grants-2010_10
- Patentnummer
- US07807692B2
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