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Imidazole-1-carboxylic acid 4-trifluoromethylbenzyl ester → 3-[3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-4-methyl-phenyl]-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester

HRID 1269535
ノート
印刷プレビュー

反応式

HRID 1269535 の反応式
C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.[CH2:11]([O:13][C:14](=[O:32])[C:15]([CH3:31])([O:17][C:18]1[CH:23]=[C:22]([CH:24]2[CH2:29][CH2:28][CH2:27][NH:26][CH2:25]2)[CH:21]=[CH:20][C:19]=1[CH3:30])[CH3:16])[CH3:12].[F:33][C:34]([F:51])([F:50])[C:35]1[CH:49]=[CH:48][C:38]([CH2:39][O:40][C:41](N2C=CN=C2)=[O:42])=[CH:37][CH:36]=1>C(OCC)(=O)C>[F:33][C:34]([F:50])([F:51])[C:35]1[CH:49]=[CH:48][C:38]([CH2:39][O:40][C:41]([N:26]2[CH2:27][CH2:28][CH2:29][CH:24]([C:22]3[CH:21]=[CH:20][C:19]([CH3:30])=[C:18]([O:17][C:15]([C:14]([O:13][CH2:11][CH3:12])=[O:32])([CH3:31])[CH3:16])[CH:23]=3)[CH2:25]2)=[O:42])=[CH:37][CH:36]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 68882567Imidazole-1-carboxylic acid 4-trifluoromethylbenzyl esterHCID 688846382-Methyl-2-(2-methyl-5-piperidin-3-yl-phenoxy)-propionic acid ethyl ester l-tartaric acid salt

生成物 1

HCID 688868503-[3-(1-Ethoxycarbonyl-1-methyl-ethoxy)-4-methyl-phenyl]-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester収率 91%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

2-methyl-2-(2-methyl-5-piperidin-3-yl-phenoxy)-propionic acid ethyl ester L-tartaric acid salt (Example 11; 155 mg, 0.34 mmol) was dissolved in 50 mL ethyl acetate and washed with 50 mL saturated aqueous NaHCO3. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The resultant oil was taken up in 3 mL toluene and imidazole-1-carboxylic acid 4-trifluoromethyl-benzyl ester (92 mg, 0.34 mmol) was added. The reaction was stirred for 18 h at room temperature under nitrogen. The reaction was flash chromatographed with 15% ethyl acetate/hexanes to yield 157 mg (91%) of the desired 3-[3-(1-ethoxycarbonyl-1-methyl-ethoxy)-4-methyl-phenyl]-piperidine-1-carboxylic acid 4-trifluoromethyl-benzyl ester as a clear oil.

後処理

  1. washwashed with 50 mL saturated aqueous NaHCO3
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customchromatographed with 15% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-a4f4db91668049c393a02b347ba920f2
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07199243B2

反応ノート

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