Ethyl Acrylate → 3-[4-(1-tert-Butoxycarbonylamino-ethyl)-phenyl]-acrylic acid ethyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].CN(C1CCCCC1)C1CCCCC1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[C:45]([O:49][CH2:50][CH3:51])(=[O:48])[CH:46]=[CH2:47]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH2:50]([O:49][C:45](=[O:48])[CH:46]=[CH:47][C:13]1[CH:14]=[CH:15][C:10]([CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])[CH3:9])=[CH:11][CH:12]=1)[CH3:51]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a mixture of [1-(4-bromo-phenyl)-ethyl]-carbamic acid tert-butyl ester (3.0 g, 10 mmol), tris(dibenzylideneacetone)dipalladium (0.55 g, 0.6 mmol), and N -methyldicyclohexylamine (2.1 mL, 10 mmol) was purged nitrogen followed by the addition of 1,4-dioxane (20 mL) and tri-tert-butylphospine (0.24 g, 1.2 mmol). The mixture was again purged with nitrogen and the ethyl acrylate (2.16 mL, 20 mmol) was added. The mixture was heated to 80° C. for 30 min, poured into water (100 mL) and extracted with ethyl acetate (150 mL). The organic layer was separated, washed again with water, dried over magnesium sulfate, concentrated and chromatographed on silica gel using 2:1 hexanes/ethyl acetate to afford a light-brown oil. M+1=320.
Workup
- customwas purged nitrogen
- customThe mixture was again purged with nitrogen
- extractionextracted with ethyl acetate (150 mL)
- customThe organic layer was separated
- washwashed again with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customchromatographed on silica gel using 2:1 hexanes/ethyl acetate
- customto afford a light-brown oil
Sources & evidence
- ORD record
- ord-3548fe0a340042d59fd4d020a5eaab90
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504403B2
Reaction notes
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