Lithium diisopropylamide → HCID 178455343, Verbindung

HRID 2235237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2235237
[C:1]([Si:5]([CH3:20])([CH3:19])[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[Li+].CC([N-]C(C)C)C.[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([Cl:46])[C:40]([CH2:44]Br)=[C:41]([Cl:43])[CH:42]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1.C([O-])(O)=O.[Na+].CCOC(C)=O>[CH2:29]([O:36][C:37]1[CH:38]=[C:39]([Cl:46])[C:40]([CH2:44][CH:15]2[CH2:16][CH2:17][N:13]([C@H:10]3[CH2:9][CH2:8][C@@H:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:20])[CH3:19])[CH2:12][CH2:11]3)[C:14]2=[O:18])=[C:41]([Cl:43])[CH:42]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Komponenten

7

Edukt 3

HCID 2724682Lithium diisopropylamideHCID 592994282-Bromomethyl-1,3-dichloro-5-benzyloxy-benzeneHCID 178455336HCID 178455336, Verbindung

Produkt 1

HCID 178455343HCID 178455343, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Dissolve 2 g (6.7 mmol) cis-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (Preparation 69) in 40 mL of dry THF and cool to −78° C. Add 4 mL 2M LDA dropwise and continue stirring at −78° C. for 30 minutes. Allow the mixture to warm to −40° C. for 0.5 hour then re-cool to −78° C. Add a solution of 2.3 g (6.6 mmol) of the 5-benzyloxy-2-bromomethyl-1,3-dichloro-benzene (Preparation 70) in 20 mL dry THF dropwise, remove the cooling bath and stir the reaction at ambient temperature for 72 hours. Dilute the mixture with 100 mL saturated aqueous NaHCO3 and 50 mL EtOAc. Separate the layers, dry the organic layer with MgSO4 and concentrate under vacuum to an oil. Purify by chromatography using 80/20 Hex/EtOAc to recover 2.3 g (59%) of the title compound as an oil.

Aufarbeitung

  1. temperatureAllow the mixture to warm to −40° C. for 0.5 hour
  2. temperaturethen re-cool to −78° C
  3. customremove the cooling bath
  4. stirringstir
  5. customthe reaction at ambient temperature for 72 hours
  6. customSeparate the layers
  7. dry with materialdry the organic layer with MgSO4
  8. concentrationconcentrate under vacuum to an oil
  9. customPurify by chromatography
  10. customto recover 2.3 g (59%) of the title compound as an oil

Quellen und Nachweise

ORD-Eintrag
ord-5492454547e04ca7ae1c57dce96cf43e
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713979B2

Notizen zur Reaktion

Wird geladen…