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Acetonitrile → N-[(1RS,2SR)-1-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-2-hydroxyethyl]-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide

HRID 1610720
ノート
印刷プレビュー

反応式

HRID 1610720 の反応式
[NH2:1][CH:2]([CH2:12]CC1C=CC(C(C)(C)C)=CC=1)[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)[OH:4].[C:24]1([C:35]([OH:37])=O)[CH:25]=[CH:26][CH:27]=[C:28]2[CH2:34][CH2:33][CH2:32][CH:31]=[CH:30][C:29]=12.O.ON1[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][C:43]=2N=N1.Cl.C(N=C=N[CH2:55][CH2:56][CH2:57]N(C)C)C.[C:61](#N)C>C(OCC)(=O)C>[C:56]([C:43]1[CH:48]=[CH:47][C:46]([CH2:12][CH:2]([NH:1][C:35]([C:24]2[CH:25]=[CH:26][CH:27]=[C:28]3[CH2:34][CH2:33][CH2:32][CH:31]=[CH:30][C:29]=23)=[O:37])[CH:3]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[OH:4])=[CH:45][CH:44]=1)([CH3:57])([CH3:61])[CH3:55]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 6342AcetonitrileHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22261419(1RS,2RS)-2-amino-3-[4-(tert-butyl)benzyl]-1-(4-fluorophenyl)propan-1-olHCID 222620106,7-dihydro-5H-benzo[a]cycloheptene-1-carboxylic acid

生成物 1

HCID 22262326
N-[(1RS,2SR)-1-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-2-hydroxyethyl]-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide
収率 67%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (1RS,2RS)-2-amino-3-[4-(tert-butyl)benzyl]-1-(4-fluorophenyl)propan-1-ol (0.41 g, 1.36 mmol) in acetonitrile (10 ml) were added 6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxylic acid (0.20 g, 1.05 mmol) and 1-hydroxybenzotriazole monohydrate (0.16 g, 1.05 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.20 g, 1.05 mmol) was finally added. The mixture was stirred at room temperature for 3 days. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1, 2:1). Recrystallization (hexane-ethyl acetate) gave N-[(1RS,2SR)-1-(4-tert-butylbenzyl)-2-(4-fluorophenyl)-2-hydroxyethyl]-6,7-dihydro-5H-benzo[a]cycloheptene-1-carboxamide (0.43 g, 67%) as colorless crystals.

後処理

  1. additionwas finally added
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1, 2:1)
  7. customRecrystallization (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-663e705dae894f2f896ac1a54129cd0f
出典データセット
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06982348B2

反応ノート

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