Methanol → 3-(Allyloxy)-1-(3-methoxyphenyl)propan-1-amine

HRID 501684ノート

反応式

HRID 501684 の反応式
[CH2:1]([O:4][CH2:5][CH2:6][CH:7]([NH:16]C(=O)C(F)(F)F)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].CO>O>[CH2:1]([O:4][CH2:5][CH2:6][CH:7]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1)[NH2:16])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86622320N-(3-(allyloxy)-1-(3-methoxyphenyl)propyl)-2,2,2-trifluoroacetamide

生成物 1

HCID 684659353-(Allyloxy)-1-(3-methoxyphenyl)propan-1-amine収率 92%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Step R (3): N-(3-(Allyloxy)-1-(3-methoxyphenyl)propyl)-2,2,2-trifluoroacetamide from step R (2) (610 mg, 1.92 mmol), potassium carbonate (1.33 g, 9.26 mmol), methanol (50 mL) and H2O (4 mL) were heated to reflux for 16 h. The mixture was concentrated in vacuo. H2O was added, and the aqueous layer was extracted several times with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo to afford 390 mg (92% yield) of 3-(allyloxy)-1-(3-methoxyphenyl)propan-1-amine as a pale-yellow oil. The crude mixture was used without further purification. LC-MS (M+H)+=222.95; 1H NMR (300 MHz, CDCl3) δ ppm 1.82-2.18 (m, 2H) 3.23-3.54 (m, 3H) 3.72-3.82 (m, 3H) 3.83-4.00 (m, 2H) 4.14 (t, J=6.95 Hz, 1H) 5.08-5.31 (m, 2H) 5.76-5.95 (m, 1H) 6.71-6.86 (m, 1H) 6.86-6.97 (m, 1H) 7.14-7.29 (m, 2H).

後処理

  1. temperatureto reflux for 16 h
  2. concentrationThe mixture was concentrated in vacuo
  3. additionH2O was added
  4. extractionthe aqueous layer was extracted several times with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6bb2d28c33244a168a95d9051a03102c
出典データセット
uspto-grants-2010_08
特許番号
US07772221B2

反応ノート

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