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

HRID 658811ノート

反応式

HRID 658811 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
45 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0c33eeea74b345cb872f1cf8bc252048
出典データセット
uspto-grants-2011_12
特許番号
US08076516B2

反応ノート

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