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

HRID 1993377노트

반응식

HRID 1993377 반응식
[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]

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 22277759Boron tribromide dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b8e2c54765d84391aa069bb7d0c676b9
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652009B2

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