Pyrrolidine → 1-[(4-Bromophenoxy)acetyl]pyrrolidine

HRID 500181

反応式

HRID 500181 の反応式
C(Cl)(=O)C(Cl)=O.[Br:7][C:8]1[CH:18]=[CH:17][C:11]([O:12][CH2:13][C:14]([OH:16])=O)=[CH:10][CH:9]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>C(Cl)Cl.CN(C)C=O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:16])=[CH:17][CH:18]=1

参加物

6

反応物 3

HCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 74657p-Bromophenoxyacetic acid

生成物 1

HCID 7876791-[(4-Bromophenoxy)acetyl]pyrrolidine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

Oxalyl chloride (0.5 mL, 5.9 mmol) was added to a suspension of (4-bromophenoxy)acetic acid (0.462 g, 2.0 mmol) in methylene chloride (10 mL) and 2 drops of N,N-dimethylformamide. The mixture was stirred at RT for 2 h. The solvent was evaporated under reduced pressure. The residue was diluted with methylene chloride (10 mL), cooled with ice-water bath, and 1M of sodium hydroxide aqueous solution (3.0 mL) was added. To the mixture was added pyrrolidine (167 μL, 2.0 mmol). The mixture was stirred and allowed to warm to RT. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was directly used in next step without further purification (550 mg, 96.7%). LCMS: (M+H)=286.0/284.0

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with methylene chloride (10 mL)
  3. temperaturecooled with ice-water bath
  4. addition1M of sodium hydroxide aqueous solution (3.0 mL) was added
  5. stirringThe mixture was stirred
  6. temperatureto warm to RT
  7. customThe organic layer was separated
  8. washwashed with water and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue was directly used in next step without further purification (550 mg, 96.7%)

出典と根拠

ORDレコード
ord-746b17a2070148b2ad2b77f13ddfa069
出典データセット
uspto-grants-2010_08
特許番号
US07767675B2

関連ノート

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