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

HRID 1993377Notes

Reaction equation

HRID 1993377 reaction equation
[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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 22277759Boron tribromide dichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b8e2c54765d84391aa069bb7d0c676b9
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

Loading…