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Triethylamine → 3-Methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethoxy)phenyl]piperidine-1,3-dicarboxylate

HRID 661200
ノート
印刷プレビュー

反応式

HRID 661200 の反応式
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[F:14][C:15]([F:34])([F:33])[O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][NH:27][CH2:26][CH:25]([C:29]([O:31][CH3:32])=[O:30])[CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl>[F:34][C:15]([F:14])([F:33])[O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:28][N:27]([C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[CH2:26][CH:25]([C:29]([O:31][CH3:32])=[O:30])[CH2:24]2)=[CH:19][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 58002737Methyl 5-(4-(trifluoromethoxy)phenyl)piperidine-3-carboxylate

生成物 1

HCID 580025493-Methyl 1-(4-nitrophenyl) 5-[4-(trifluoromethoxy)phenyl]piperidine-1,3-dicarboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

At 0° C., 5.32 g (26.4 mmol) of 4-nitrophenyl chloroformate were added slowly to 8.0 g (26.4 mmol) of methyl 5-(4-(trifluoromethoxy)phenyl)piperidine-3-carboxylate and 5.34 g (26.3 mmol) of triethylamine in 666 ml of dichloromethane. The mixture was stirred at RT for 2 h. For workup, the reaction mixture was washed first with saturated aqueous sodium hydrogencarbonate solution, then with water. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2->1:1). Yield: 7.32 g (54% of theory)

後処理

  1. washFor workup, the reaction mixture was washed first with saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2->1:1)

出典と根拠

ORDレコード
ord-fa4e461019b44a24b11f69a92aa2baba
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08084469B2

反応ノート

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