Boron tribromide → (R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-one

HRID 1972246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972246
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24]C)[CH:19]=4)[CH2:16][CH2:15][C:14]3=[O:26])=[N:11][CH:12]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[N:8]=[CH:9][C:10]([N:13]3[C@@H:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=4)[CH2:16][CH2:15][C:14]3=[O:26])=[N:11][CH:12]=2)=[CH:27][CH:28]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 59485648(R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-methoxyphenyl)pyrrolidin-2-one

Produkt 1

HCID 59485583(R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-oneAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of (R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-methoxyphenyl)pyrrolidin-2-one (286 mg, 0.72 mmol), DCM (10 mL) and BBr3 (1M in DCM, 4 mL) is stirred at room temperature for 1 h. The reaction mixture is then diluted with DCM (120 mL), washed with saturated NaHCO3 (20 mL) and brine (20 mL) and dried over Na2SO4. After concentrating, the residue is purified on silica gel (0-33% ethyl acetate in hexane) to give (R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-one (276 mg, 100%) as a white solid. HPLC-MS calculated for C20H16ClN3O3 (M+H+) 382.09, found 382.10.

Aufarbeitung

  1. washwashed with saturated NaHCO3 (20 mL) and brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationAfter concentrating
  4. customthe residue is purified on silica gel (0-33% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-3ced979531644e578809dc8338355e15
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431607B2

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