2-{6-Methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde → 1-{2-[4-(10-methoxy-5H,7H-6-oxa-12-thia-dibenzo[a,e]azulen-7-yl)-phenoxy]-ethyl)-piperidine

HRID 916857ノート

反応式

HRID 916857 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([C:17](=[O:33])[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:20][CH:19]=3)=[C:15]([C:34]3[CH:41]=[CH:40][CH:39]=[CH:38][C:35]=3[CH:36]=O)[S:14][C:13]=2[CH:42]=1>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]3[CH:17]([C:18]4[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][N:27]5[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]5)=[CH:22][CH:23]=4)[O:33][CH2:36][C:35]4[CH:38]=[CH:39][CH:40]=[CH:41][C:34]=4[C:15]=3[S:14][C:13]=2[CH:42]=1

参加物

4

反応物 2

HCID 179870572-{6-Methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehydeHCID 21226445Aluminium lithium hydride

生成物 1

HCID 100968891-{2-[4-(10-methoxy-5H,7H-6-oxa-12-thia-dibenzo[a,e]azulen-7-yl)-phenoxy]-ethyl)-piperidine収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Add LAH solution (1M/THF) to a solution of 2-{6-methoxy-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-2-yl}-benzaldehyde (410 mg, 0.82 mmol) in THF (5 mL) at r.t. until LCMS analysis indicates complete consumption of starting material. Dilute the mixture with THF (10 mL) and water (2 mL), followed by cautious addition of HCl(5 M) to pH 1. Heat gently for 10 min. Dilute with CH2Cl2 and quench with aq. NaHCO3. Wash the organic phase with water and brine, dry over MgSO4, filter and concentrate. Purify the crude product by flash chromatography (0-10% (2M NH3 in MeOH)/CH2Cl2) to afford 1-{2-[4-(10-methoxy-5H,7H-6-oxa-12-thia-dibenzo[a,e]azulen-7-yl)-phenoxy]-ethyl}-piperidine (266 mg, 67%).

後処理

  1. customconsumption of starting material
  2. additionDilute the mixture with THF (10 mL) and water (2 mL)
  3. additionfollowed by cautious addition of HCl(5 M) to pH 1
  4. temperatureHeat gently for 10 min
  5. additionDilute with CH2Cl2
  6. customquench with aq. NaHCO3
  7. washWash the organic phase with water and brine
  8. dry with materialdry over MgSO4
  9. filtrationfilter
  10. concentrationconcentrate
  11. customPurify the crude product by flash chromatography (0-10% (2M NH3 in MeOH)/CH2Cl2)

出典と根拠

ORDレコード
ord-dbe0e6d0d191434687b79260d1f15109
出典データセット
uspto-grants-2007_09
特許番号
US07271264B2

反応ノート

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