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

HRID 1057782Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057782
[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.[CH3:25][Mg]Br>C1COCC1>[OH:1][C:2]1([CH3:25])[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 178418573HCID 178418573, Verbindung

Produkt 1

HCID 98590064'-[3-(3-Hydroxy-3-methyl-1-pyrrolidinyl)propoxy][1,1'-biphenyl]-4-carbonitrileAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product from Example 154 (130 mg, 0.41 mmol) in dry THF (6 mL) under an atmosphere of nitrogen at 0° C. was treated with a 3.0M solution of methylmagnesium bromide (0.82 mmol). After warming to ambient temperature and stirring for 2 hours, the mixture was quenched with 3 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 (55% yield).

Aufarbeitung

  1. customthe mixture was quenched with 3 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-7cd8c6ebeced4e1b8fc6b62fec823fe3
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515013B2

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