Sodium Hydroxide → 2-(2-{4-[1-(3-[1,3]dioxolan-2-yl-propyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic Acid

HRID 457789

反応式

HRID 457789 の反応式
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH:16]([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][CH:20]=2)[CH2:15][CH2:14]1.[H-].[Na+].Cl[CH2:32][CH2:33][CH2:34][CH:35]1[O:39][CH2:38][CH2:37][O:36]1.[OH-].[Na+]>CN(C=O)C.C(O)C>[O:36]1[CH2:37][CH2:38][O:39][CH:35]1[CH2:34][CH2:33][CH2:32][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([CH:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][O:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:3]([OH:28])=[O:2])[CH2:14][CH2:15]2)=[CH:20]1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 5520722-(3-Chloropropyl)-1,3-dioxolaneHCID 11440344methyl 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoate

生成物 1

HCID 102275642-(2-{4-[1-(3-[1,3]dioxolan-2-yl-propyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic Acid

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒3 回

実験手順

A solution of 2.75 g (7 mmol) of 2-{2-[4-(1H-indol-3-yl)-piperidin-1-yl]-ethoxy}-benzoic acid methyl ester (prepared as in Example 1, part D) in 10 mL of anhydrous DMF was added to a suspension of 0.36 g (9.1 mmol) of a NaH (60% dispersion in mineral oil) in 5 mL of anhydrous DMF under an inert atmosphere. After stirring for 30 minutes at room temperature, a solution of 1.1 mL (8.4 mmol) of 2-(3-chloro-propyl)-[1,3]dioxolane in 3 mL of DMF was added. The crude mixture was stirred at room temperature for 16 hours and the solvent was removed under reduced pressure. The residue obtained was dissolved with 150 mL of ethanol and 6 mL of a 2N NaOH aqueous solution were added. After 12 h at room temperature, the solvent was removed under reduced pressure. The crude mixture was dissolved with 50 mL of water and neutralised with a 2N HCl aqueous solution. The crude mixture was purified by flash chromatography over silica gel affording 0.83 g (29% of yield) of the expected product.

後処理

  1. customthe solvent was removed under reduced pressure
  2. customThe residue obtained
  3. additionwere added
  4. waitAfter 12 h at room temperature
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe crude mixture was dissolved with 50 mL of water and neutralised with a 2N HCl aqueous solution
  7. customThe crude mixture was purified by flash chromatography over silica gel affording 0.83 g (29% of yield) of the expected product

出典と根拠

ORDレコード
ord-06bb16c5ca144ad3a790b4f00ec27b91
出典データセット
uspto-grants-2007_03
特許番号
US07189741B2

関連ノート

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