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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 2407261
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인쇄 미리보기

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HRID 2407261 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-aae0f27e0dba4589a7da15a8ee939dfd
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809536B2

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