Hydrochloric Acid → HCID 86629974、化合物

HRID 657636ノート

反応式

HRID 657636 の反応式
[H-].[Na+].[CH:3](OC)=[O:4].[CH3:7][C@H:8]1[CH2:13][C@H:12]([CH3:14])[CH2:11][N:10]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=2)[CH2:9]1.Cl>O1CCCC1>[CH3:14][C@H:12]1[CH2:13][C@H:8]([CH3:7])[CH2:9][N:10]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH2:26][CH:3]=[O:4])=[CH:21][CH:20]=2)[CH2:11]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 9795992HCID 9795992、化合物

生成物 1

HCID 86629974HCID 86629974、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of sodium hydride (82 mg, 60% in paraffin) are added methyl formate (150 μL) and a solution of trans-3,5-dimethyl-1-[3-(4-acetylphenoxy)propyl]piperidine (610 mg) in tetrahydrofuran (0.4 mL). The mixture is stirred for two hours at room temperature then hydrolysed with a 1N aqueous hydrochloric acid solution keeping the pH alkaline. The solution is extracted twice with ethyl acetate. The extracts are pooled, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with a gradient dichloromethane/methanol from 100/0 to 95/5. Fractions containing the expected product are pooled, concentrated under reduced pressure to give 100 mg of trans-3,5-dimethyl-1-{3-[4-(3-oxopropanoyl)phenoxy]propyl}piperidine as a pale yellow oil that is used rapidly, without further purification in the next step.

後処理

  1. extractionThe solution is extracted twice with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by chromatography over silica gel with a gradient dichloromethane/methanol from 100/0 to 95/5
  5. additionFractions containing the expected product
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9b3feb5de2e74c9eaf06f8718d527bd3
出典データセット
uspto-grants-2011_12
特許番号
US08076329B2

反応ノート

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