4'-[3-(3-Oxo-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile → 4'-[3-(3-Hydroxy-3-isopropyl-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrile

HRID 1057783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057783
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=3)=[CH:13][CH:12]=2)[CH2:3]1.[CH:25]([Mg]Cl)([CH3:27])[CH3:26]>C1COCC1>[OH:1][C:2]1([CH:25]([CH3:27])[CH3:26])[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[CH2:3]1

Komponenten

4

Edukt 2

HCID 99230964'-[3-(3-Oxo-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrileHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 102922444'-[3-(3-Hydroxy-3-isopropyl-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrileAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product from Example 154 (147 mg, 0.46 mmol) in dry THF (10 mL) under an atmosphere of nitrogen at 0° C. was treated with a 2.0M solution of isopropylmagnesium chloride (0.92 mmol). After warming to ambient temperature and stirring for 1 hour, the mixture was quenched with 5 mL of cold saturated ammonium chloride solution and then the solution was partitioned between water (50 mL) and dichloromethane (50 mL). The organic layer was washed with brine (50 mL), dried over sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1) to provide the title compound (75% yield).

Aufarbeitung

  1. customthe mixture was quenched with 5 mL of cold saturated ammonium chloride solution
  2. customthe solution was partitioned between water (50 mL) and dichloromethane (50 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customthe residue purified by chromatography (CHCl3:MeOH:NH4OH, 9:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-ba363cb1d233475abe5840b0da0c4d17
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515013B2

Notizen zur Reaktion

Wird geladen…