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Hydrogen Bromide → 3-[(R*)-1-((S)-6-Benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol

HRID 453767
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인쇄 미리보기

반응식

HRID 453767 반응식
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]2[O:13][C@@H:14]([CH2:17]OS(C)(=O)=O)[CH2:15][O:16][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][C@H:27]([C:31]2[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=2)[CH2:26]1.Br.C([O-])(O)=O.[Na+]>C(#N)C>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]2[O:13][C@@H:14]([CH2:17][N:25]3[CH2:30][CH2:29][CH2:28][C@H:27]([C:31]4[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=4)[CH2:26]3)[CH2:15][O:16][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 12937952Phenol, 3-(3R)-3-piperidinyl-HCID 86644715(R)-(6-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl methanesulfonate

생성물 1

HCID 251751693-[(R*)-1-((S)-6-Benzyloxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl)-piperidin-3-yl]-phenol

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
150 °C

실험 절차

To a solution of methanesulfonic acid (R)-6-benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl ester (129 mg, 0.368 mmol) and (R*)-3-(piperidin-3-yl)phenol.HBr (100 mg, 0.387 mmol) in acetonitrile was added solid KI (40 mg) and NaHCO3 (98 mg 1.162 mmol). The mixture was heated under microwave irradiation at 150° C. for 1 h. Solid material was filtered and the solvent was evaporated under reduced pressure. The residue was dissolved to DCM and washed twice with water and brine. The organic phase was dried (Na2SO4), and evaporated in vacuo. The residue was purified by flash column chromatography (EtOAc/heptane) to give the desired product (66.2 mg).

후처리

  1. filtrationSolid material was filtered
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved to DCM
  4. washwashed twice with water and brine
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by flash column chromatography (EtOAc/heptane)

출처 및 근거

ORD 기록
ord-61a6f31130af4340ae8e00725be6dba6
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492549B2

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