Hydrochloric Acid → 2-[3-(2-Amino-ethyl)-phenoxy]-2-methyl-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]([CH3:19])([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10](/[CH:14]=[CH:15]/[N+:16]([O-])=O)[CH:9]=1)[CH3:6])[CH3:2].Cl>C(O)C.[Pd].C>[CH2:1]([O:3][C:4](=[O:20])[C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][NH2:16])[CH:9]=1)([CH3:19])[CH3:6])[CH3:2]Participants
5
Procedure
7.82 g (28.0 mmol) of 2-methyl-2-[3-((E)-2-nitro-vinyl)-phenoxy]-propionic acid ethyl ester was dissolved in 150 ml ethanol; 6.2 ml (39.7 mmol) hydrochloric acid in ethanol and 1.6 g of Pd-charcoal (10%) were added and the reaction mixture was then hydrogenated under 1 atm of H2-pressure during 5 hours. It was subsequently filtered (Celite), the filter cake was washed twice with ethanol and filtrate was evaporated. The residue was then partitioned between crashed ice/Na2CO3-solution/MeCl2 and extracted twice with MeCl2; the organic phases were washed with water, dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (SiO2, MeCl2/MeOH) to give 4.36 g of the title compound as yellow oil.
Workup
- filtrationIt was subsequently filtered (Celite)
- washthe filter cake was washed twice with ethanol and filtrate
- customwas evaporated
- customThe residue was then partitioned
- extractionextracted twice with MeCl2
- washthe organic phases were washed with water
- dry with materialdried (MgSO4)
- customevaporated
- customThe crude product was purified by flash chromatography (SiO2, MeCl2/MeOH)
Sources & evidence
- ORD record
- ord-07d18b8ed7344e259a44c7f9a9898076
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115611B2
Reaction notes
Loading…