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

HRID 501680Notes

Reaction equation

HRID 501680 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fc82fa7f2fc84f3d91050a5cfdefe9b0
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

Loading…