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

HRID 1172337노트

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HRID 1172337 반응식
[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

참가 물질

6

반응물 4

HCID 8471Triethylamine2회HCID 31297Methanesulfonyl chlorideHCID 79341Piperidin-4-olHCID 68771799HCID 68771799, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-ced110350a19409e837d9918ca383962
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834012B2

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