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

HRID 2046700노트

반응식

HRID 2046700 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 21908982Water methylene chloride용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-56354329337f48e7886261b327275041
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592444B2

반응 노트

불러오는 중…