N-(2-phenylethyl)acetamide → Methyl alpha,alpha-dimethyl-beta-oxo-beta-[4-(2-acetamidoethyl)-phenyl]-propionate
Reaction equation
Cl.CC(C)(CC1C=CC(CCN)=CC=1)C(OCC)=O.[C:20]([NH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:22])[CH3:21].[Cl-].[CH3:33][O:34][C:35](=[O:42])[C:36]([CH3:41])([CH3:40])[C:37](O)=[O:38]>>[CH3:40][C:36]([CH3:41])([C:37](=[O:38])[C:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH2:24][NH:23][C:20](=[O:22])[CH3:21])=[CH:27][CH:28]=1)[C:35]([O:34][CH3:33])=[O:42]Participants
Reactant 3
Product 1
Procedure
The ethyl α,α-dimethyl-β-[4-(2-aminoethyl)-phenyl]-propionate hydrochloride (m.p. 113°-117° C.) used as starting material is prepared in the following manner: N-acetylphenethylamine is reacted with dimethylmalonic acid methyl ester chloride according to Friedel-Crafts method to give methyl α,α-dimethyl-β-oxo-β-[4-(2-acetamidoethyl)-phenyl]-propionate (b.p. 215°-220° C./0.1 mm.Hg.), this then reduced, via methyl α,α-dimethyl-β-hydroxy-β-[4-(2-acetamidoethyl)-phenyl]-propionate (m.p. 120°-123° C.) to give methyl α,α-dimethyl-β-[4-(2-acetamidoethyl)-phenyl]-propionate (b.p. 180°-190° C./0.1 mm Hg.), saponified to give α,α-dimethyl-β-[4-(2-aminoethyl)-phenyl]-propionic acid hydrochloride (m.p. 230°-235° C.) and thereafter esterified to give the desired ethyl ester hydrochloride.
Workup
- customis prepared in the following manner
Sources & evidence
- ORD record
- ord-6292f4c6c3fb4dbeb36473ef78a73e93
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04238506
Reaction notes
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