Triethylamine → 1-{[trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}piperidin-4-ol

HRID 1172337ノート

反応式

HRID 1172337 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([N+:14]([O-:16])=[O:15])[CH2:12][CH:11]=[CH:10][CH2:9]1.CS([Cl:21])(=O)=O.[CH2:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])C.N1CC[CH:32]([OH:35])CC1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:21])[CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([N+:14]([O-:16])=[O:15])[CH2:12][C:11]([CH2:22][N:24]2[CH2:27][CH2:28][CH:32]([OH:35])[CH2:26][CH2:25]2)=[CH:10][CH2:9]1

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 31297Methanesulfonyl chlorideHCID 79341Piperidin-4-olHCID 68771799HCID 68771799、化合物

生成物 1

HCID 687683961-{[trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}piperidin-4-ol収率 70.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a cold (0° C.) CH2Cl2 (1 mL) solution of Example 1A (61 mg, 0.2 mmol), methanesulfonyl chloride (0.017 mL, 0.22 mmol) and triethylamine (0.035 mL, 0.25 mmol) were added. After it was stirred at 0° C. for five minutes, more triethylamine (0.035 mL, 0.25 mmol) and piperidin-4-ol (25 mg, 0.24 mmol) were added to the reaction mixture. The reaction was allowed to warm from 0° C. to room temperature overnight. It was diluted with CH2Cl2, washed with water and brine, dried over sodium sulfate, filtered, concentrated under reduced pressure and purified by high pressure liquid chromatography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (54 mg, 69%). MS (DCI) m/z 386 (M+H)+.

後処理

  1. temperatureto warm from 0° C. to room temperature overnight
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified by high pressure liquid chromatography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)

出典と根拠

ORDレコード
ord-ced110350a19409e837d9918ca383962
出典データセット
uspto-grants-2010_11
特許番号
US07834012B2

反応ノート

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