Methanol → (1R)-2-Allyloxy-1-phenyl-ethanamine

HRID 501680노트

반응식

HRID 501680 반응식
[CH2:1]([O:4][CH2:5][C@H:6]([NH:13]C(=O)C(F)(F)F)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].CO>O>[CH2:1]([O:4][CH2:5][C@@H:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:13])[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86622318(R)-N-(2-(allyloxy)-1-phenylethyl)-2,2,2-trifluoroacetamide

생성물 1

HCID 68465142(1R)-2-Allyloxy-1-phenyl-ethanamine수율 54.4%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Step Q (3): (R)-N-(2-(Allyloxy)-1-phenylethyl)-2,2,2-trifluoroacetamide (3.0 g, 11.0 mmol) from step Q (2), potassium carbonate (7.59 g, 55 mmol), methanol (300 mL) and H2O (20 mL) were heated to reflux for 16 h. The mixture was concentrated in vacuo. Water was added, and the aqueous layer was repeatedly extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo to afford 1.06 g (54% yield) of (R)-2-(allyloxy)-1-phenylethanamine as a yellow oil. The crude mixture was used without further purification. LC-MS (M+H)+=178.18. 1H NMR (300 MHz, CDCl3) δ ppm 2.02 (s, 2H) 3.38 (t, J=9.15 Hz, 1H) 3.48-3.63 (m, 1H) 3.99 (d, J=5.49 Hz, 2H) 4.19 (dd, J=9.15, 3.66 Hz, 1H) 5.05-5.31 (m, 2H) 5.74-5.99 (m, 1H) 7.15-7.42 (m, 5H).

후처리

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

출처 및 근거

ORD 기록
ord-fc82fa7f2fc84f3d91050a5cfdefe9b0
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772221B2

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