2-Bromo-1,2-diphenylethan-1-one → 2-Oxo-1,2-diphenylethyl 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylate

HRID 380128

反応式

HRID 380128 の反応式
[Na].[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[C:21]([OH:23])=[O:22])=[O:14])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:27]1([C:33]([CH:35](Br)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:34])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C.S(=O)(=O)(O)O>[CH2:2]([O:9][C:10]1[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=1)[C:13]([N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[C:21]([O:23][CH:35]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:33](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:22])=[O:14])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 3

HCID 1026302-Bromo-1,2-diphenylethan-1-oneHCID 5360545SodiumHCID 183674161-(3-Benzyloxybenzoyl)-2-piperidinecarboxylic acid

生成物 1

HCID 542478562-Oxo-1,2-diphenylethyl 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylate収率 28.4%

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

Sodium (54 mg) was dissolved in ethanol (8.0 ml), and then 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylic acid (665 mg), conc. sulfuric acid (1 drop), and desyl bromide (539 mg) was successively dissolved thereto. The resulting mixture was stirred at 70° C. for 2 days, cooled to room temperature, and partitioned between ethyl acetate and 1N HCl. The organic layer was washed with 1N HCl, aqueous sodium bicarbonate, and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 2-oxo-1,2-diphenylethyl 1-(3-benzyloxybenzoyl)-2-piperidinecarboxylate (297 mg) as a pale yellow oil.

後処理

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and 1N HCl
  3. washThe organic layer was washed with 1N HCl, aqueous sodium bicarbonate, and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was chromatographed over silica gel

出典と根拠

ORDレコード
ord-969536c747cd4b3a94fb701bec284060
出典データセット
uspto-grants-2001_10
特許番号
US06300344B1

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