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

HRID 1972246ノート

反応式

HRID 1972246 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 59485583(R)-1-[5-(4-chlorophenoxy)pyrazin-2-yl]-5-(3-hydroxyphenyl)pyrrolidin-2-one収率 100.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3ced979531644e578809dc8338355e15
出典データセット
uspto-grants-2013_04
特許番号
US08431607B2

反応ノート

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