1-(3-Fluoro-4-methoxyphenyl)-4-(phenoxymethyl)pyrrolidin-2-one → 1-(3-Fluoro-4-hydroxyphenyl)-4-(phenoxymethyl)pyrrolidin-2-one

HRID 1993377ノート

反応式

HRID 1993377 の反応式
[F:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:14][CH:13]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:12][C:11]2=[O:23])[CH:5]=[CH:6][C:7]=1[O:8]C>B(Br)(Br)Br.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([N:10]2[CH2:14][CH:13]([CH2:15][O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:12][C:11]2=[O:23])[CH:5]=[CH:6][C:7]=1[OH:8]

参加物

3

反応物 1

HCID 684201161-(3-Fluoro-4-methoxyphenyl)-4-(phenoxymethyl)pyrrolidin-2-one

生成物 1

HCID 684205651-(3-Fluoro-4-hydroxyphenyl)-4-(phenoxymethyl)pyrrolidin-2-one

試薬・触媒・溶媒 1

HCID 22277759Boron tribromide dichloromethane溶媒

実験手順

A solution of 1-(3-fluoro-4-methoxyphenyl)-4-(phenoxymethyl)pyrrolidin-2-one (Step 3, 1.0 g, 3.17 mmol) in 15.85 mL of 1 M BBr3/CH2Cl2 was stirred at RT for 10 h. The solution was concentrated in vacuo and the residue was diluted with 100 mL of EtOAc. The organic phase was washed with 40 mL of satd. NaHCO3 followed by 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (5% to 60% EtOAc/hexane) to give the title compound as a light yellow foam. MS (ESI pos. ion) m/z: 302.3 (M+H). Calc'd Exact Mass for C17H16FNO3: 301.31.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. additionthe residue was diluted with 100 mL of EtOAc
  3. washThe organic phase was washed with 40 mL of satd
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (5% to 60% EtOAc/hexane)

出典と根拠

ORDレコード
ord-b8e2c54765d84391aa069bb7d0c676b9
出典データセット
uspto-grants-2010_01
特許番号
US07652009B2

反応ノート

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