Water → Tert-butyl 4-(5-bromo-2-fluorobenzoyl)-4-hydroxypiperidine-1-carboxylate

HRID 518155ノート

反応式

HRID 518155 の反応式
[Br-].[Br-].[Br-].N1C=CC=CC=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20]([C:24]2([C:30]3[CH:35]=[C:34]([Br:36])[CH:33]=[CH:32][C:31]=3[F:37])SCCCS2)([OH:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].N1C=CC=CC=1.[OH2:44]>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].C(Cl)Cl.O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][C:20]([C:24](=[O:44])[C:30]2[CH:35]=[C:34]([Br:36])[CH:33]=[CH:32][C:31]=2[F:37])([OH:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

参加物

7

反応物 4

HCID 962WaterHCID 1049PyridineHCID 113064294-[2-(5-Bromo-2-fluoro-phenyl)-[1,3]dithian-2-yl]-4-hydroxy-piperidine-1-carboxylic acid tert-butyl esterHCID 12591401Pyridine tribromide

生成物 1

HCID 11774000Tert-butyl 4-(5-bromo-2-fluorobenzoyl)-4-hydroxypiperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 21908982Water methylene chloride溶媒

実験手順

Pyridine tribromide (12.7 g, 39.6 mmol) and TBAB (850 mg, 2.64 mmol) were added to a stirred solution of 4-[2-(5-bromo-2-fluoro-phenyl)-[1,3]dithian-2-yl]-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (13 g, 26.42 mmol) and pyridine (2.07 ml, 39.63 mmol) in a mixture of DCM/water (5:1, 180 ml). After stirring for 24 h at RT, the solution was poured into water (150 ml) and the product was extracted with DCM. The combined organic layers were washed with water (400 ml), brine (400 ml), dried over Na2SO4, then filtered and evaporated. The crude product was purified by column chromatography (AcOEt/hexane:20/80) to give 9.5 g of 4-(5-bromo-2-fluoro-benzoyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester as a yellow oil.

後処理

  1. extractionthe product was extracted with DCM
  2. washThe combined organic layers were washed with water (400 ml), brine (400 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by column chromatography (AcOEt/hexane:20/80)

出典と根拠

ORDレコード
ord-a84cfa33857a46548c2db4a84ded4997
出典データセット
uspto-grants-2015_08
特許番号
US09115148B2

反応ノート

読み込み中…