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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Tert-butyl 4-{(2-hydroxyethyl)[(4-methyl-1H-imidazol-5-yl)carbonyl]amino}piperidine-1-carboxylate

HRID 1162337
ノート
印刷プレビュー

反応式

HRID 1162337 の反応式
Cl.[CH3:2][C:3]1[NH:7][CH:6]=[N:5][C:4]=1[C:8]([OH:10])=O.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C[Si](C)(C)NC(=O)C.[OH:40][CH2:41][CH2:42][NH:43][CH:44]1[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]1>C(#N)C.C(N(CC)CC)C>[OH:40][CH2:41][CH2:42][N:43]([C:8]([C:4]1[N:5]=[CH:6][NH:7][C:3]=1[CH3:2])=[O:10])[CH:44]1[CH2:49][CH2:48][N:47]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[CH2:46][CH2:45]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25989Acetamide, N-(trimethylsilyl)-HCID 757711-HydroxybenzotriazoleHCID 131606155-Methyl-1H-imidazole-4-carboxylic acid hydrochloride (1:1)HCID 23131007tert-Butyl 4-(2-hydroxyethylamino)piperidine-1-carboxylate

生成物 1

HCID 23138256
Tert-butyl 4-{(2-hydroxyethyl)[(4-methyl-1H-imidazol-5-yl)carbonyl]amino}piperidine-1-carboxylate
収率 59%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 8471Triethylamine溶媒

実験手順

5-Methylimidazole-4-carboxylic acid hydrochloride (G. Wellman et al., Synthesis, 356 (1984); 1.6 g) was suspended in acetonitrile (100 ml). HOBt (2.8 g) and WSC (3.5 g) were sequentially added thereto, and mixed at room temperature for 20 minutes (the reaction solution A). In a separate flask were dissolved tert-butyl 4-(2-hydroxyethyl)amino-1-piperidinecarboxylate (3.0 g) obtained in Example 91a), N-trimethylsilylacetamide (8.1 g) and triethylamine (5.0 ml) in acetonitrile (50 ml), and mixed at room temperature for 20 minutes (the reaction solution B). The reaction solution B was added to the reaction solution A, and mixed at room temperature for 15 hours. Acetonitrile was distilled off under reduced pressure, and then to the residue were added chloroform and water. The organic layer was collected by separation and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified with basic silica gel column (ethyl acetate:ethanol=5:1) to obtain the title compound as a colorless oil (2.0 g, 59%).

後処理

  1. additionmixed at room temperature for 15 hours
  2. distillationAcetonitrile was distilled off under reduced pressure
  3. additionto the residue were added chloroform and water
  4. customThe organic layer was collected by separation
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified with basic silica gel column (ethyl acetate:ethanol=5:1)

出典と根拠

ORDレコード
ord-1a6206433765403cbe790f6a12e6176e
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07820673B2

反応ノート

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