4-Aminophenol → Methyl 1-(4-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylate
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][O:10][C:11](=[O:19])[C:12](=[CH2:18])[CH2:13][C:14](OC)=[O:15]>CCOC(C)=O>[CH3:9][O:10][C:11]([CH:12]1[CH2:13][C:14](=[O:15])[N:1]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH2:18]1)=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
A mixture of 4-amino-phenol (3 g, 0.027 mol) and 2-methylene-succinic acid dimethyl ester (4.35 g, 0.027 mol) was heated to 110° C. for 16 h. The dark brown glass was dissolved in EtOAc and purified by silica gel chromatography (20% EtOAc/hexane to EtOAC) to give the title compound as an orange oil. MS (ESI pos. ion) m/z: 236.2 (M+H). Calc'd Exact Mass for C12H13NO4: 235.24.
Workup
- custompurified by silica gel chromatography (20% EtOAc/hexane to EtOAC)
Sources & evidence
- ORD record
- ord-3c5013ddfda1419890abab43a6d3cfd5
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652009B2
Reaction notes
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