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Cesium carbonate → 1-Boc-4-(3-bromophenoxy)piperidine

HRID 531451
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HRID 531451 반응식
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.CS(O[CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH:14]1[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 115633-BromophenolHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

생성물 1

HCID 224929571-Boc-4-(3-bromophenoxy)piperidine수율 85.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228
Dimethylformamide
용매

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온도
65 °C

실험 절차

The mixture of 3-bromophenol (2.0 g, 11.56 mmol), tert-butyl 4-((methylsulfonyl)oxy)piperidine-1-carboxylate (3.87 g, 13.872 mmol) and caesium carbonate (11.27 g, 34.68 mmol) in DMF (25 ml) was heated at 65° C. for 14 hours. Cooled to RT and diluted with ether. Ether layer was washed with water and brine, dried over sodium sulphate and distilled off the solvent to afford 3.5 g (85.3% yield) of the titled product after purification with (60/120 silica gel) column chromatography using 5% ethyl acetate in hexane as eluent. MS: m/z=356.0 (M+1).

후처리

  1. temperatureCooled to RT
  2. washEther layer was washed with water and brine
  3. dry with materialdried over sodium sulphate
  4. distillationdistilled off the solvent

출처 및 근거

ORD 기록
ord-3243a15c997043c9b651214a20e6a71a
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09353107B2

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