Potassium Carbonate → 1-(3-(3-Aminopropyl)phenyl)-3-ethylpent-1-yn-3-ol

HRID 658811노트

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HRID 658811 반응식
[CH2:1]([C:3]([OH:24])([CH2:22][CH3:23])[CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][CH2:14][NH:15]C(=O)C(F)(F)F)[CH:9]=[CH:10][CH:11]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO>[NH2:15][CH2:14][CH2:13][CH2:12][C:8]1[CH:7]=[C:6]([C:5]#[C:4][C:3]([CH2:22][CH3:23])([OH:24])[CH2:1][CH3:2])[CH:11]=[CH:10][CH:9]=1

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 86628449N-(3-(3-(3-ethyl-3-hydroxypentyl)phenyl)propyl)-2,2,2-trifluoroacetamide

생성물 1

HCID 251665411-(3-(3-Aminopropyl)phenyl)-3-ethylpent-1-yn-3-ol

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
45 °C

실험 절차

N-(3-(3-(3-ethyl-3-hydroxypentyl)phenyl)propyl)-2,2,2-trifluoroacetamide (12) (0.660 g, 1.93 mmol) was dissolved in MeOH (15 mL), and an aqueous solution of K2CO3 (0.42 g/3 mL) was added. The resulting mixture was stirred at 45° C. for 4 h. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure then partitioned between EtOAc (50 mL) and water (50 mL). The combined organics were dried over Na2SO4, and concentrated under reduced pressure. Purification by flash chromatography (80 to 100% (9:1 EtOAc: 7M NH3 in MeOH):hexanes gradient) gave 1-(3-(3-aminopropyl)phenyl)-3-ethylpent-1-yn-3-ol (13) as a light yellow oil. Yield (0.421 g, 89%): 1H NMR (400 MHz, DMSO-d6) δ 7.15-7.26 (m, 4H), 5.11 (s, 1H), 2.56 (t, J=7.6 Hz, 2H), 2.47 (t, J=5.2 Hz, 2H), 1.55-1.65 (m, 6H), 1.39 (br s, 2H), 0.97 (t, J=7.6 Hz, 6H).

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customthen partitioned between EtOAc (50 mL) and water (50 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash chromatography (80 to 100% (9:1 EtOAc: 7M NH3 in MeOH):hexanes gradient)

출처 및 근거

ORD 기록
ord-0c33eeea74b345cb872f1cf8bc252048
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076516B2

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