Sodium borohydride → 5-(4-(4-Fluoro-phenyl)-3-hydroxy-butyl)-pyrrolidin-2-one

HRID 458985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 458985
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:18])[CH2:10][CH2:11][CH:12]2[NH:16][C:15](=[O:17])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([OH:18])[CH2:10][CH2:11][CH:12]2[NH:16][C:15](=[O:17])[CH2:14][CH2:13]2)=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 4311764Sodium borohydride2×HCID 227125185-[4-(4-Fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one

Produkt 1

HCID 227124475-(4-(4-Fluoro-phenyl)-3-hydroxy-butyl)-pyrrolidin-2-oneAusbeute 75,5 %

Versuchsvorschrift

Analogous to the procedure described for Example 1A, Step B, 5-[4-(4-fluoro-phenyl)-3-oxo-butyl]-pyrrolidin-2-one (2.64 g, 10.6 mmol) was reduced with NaBH4 (400 mg, 10.5 mmol) at room temperature for 1 h. Additional NaBH4 (150 mg, 3.95 mmol) was added and the reaction mixture was stirred for 20 h. Purification by medium pressure chromatography using a solvent gradient (CH2Cl2 to 2% MeOH in CH2Cl2 to 4% MeOH in CH2Cl2) provided 5-[4-(4-fluoro-phenyl)-3-hydroxy-butyl]-pyrrolidin-2-one (2.01 g). 1H NMR (CDCl3) δ7.14 (m, 2H), 6.98 (m, 2H), 6.78 (m, 1H), 3.76 (m, 1H), 3.65 (m, 1H), 2.76 (m, 1H), 2.64 (m, 1H), 2.32–2.18 (m, 4H), 1.72–1.47 (m, 5H).

Aufarbeitung

  1. customPurification by medium pressure chromatography

Quellen und Nachweise

ORD-Eintrag
ord-09b27c4598e14ad38432636324f4e9eb
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192979B2

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