Sodium Carbonate → 1-(3,4,5-Trimethoxybenzoyl)-3-(phenylmethyl)-3-(2-hydroxyethyl)pyrrolidine
Reaction equation
[C:1]1([CH2:7][C:8]2([CH2:13][CH2:14][OH:15])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C.O.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([O:42][CH3:43])[C:39]=1[O:40][CH3:41])[C:34](Cl)=[O:35]>C(OCC)(=O)C>[CH3:43][O:42][C:38]1[CH:37]=[C:33]([CH:32]=[C:31]([O:30][CH3:29])[C:39]=1[O:40][CH3:41])[C:34]([N:10]1[CH2:11][CH2:12][C:8]([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:13][CH2:14][OH:15])[CH2:9]1)=[O:35]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Combine 3-(phenylmethyl)-3-(2-hydroxyethyl)pyrrolidine (3.94 mmol) and sodium carbonate (0.21 g, 2.00 mmol) in 1/1 ethyl acetate/water (50 mL). Cool the reaction mixture to 0° C. with an ice bath. Add 3,4,5-trimethoxybenzoyl chloride (0.83 g, 3.58 mmol). Warm to ambient temperature. After 18 hours, separate the layers and extract the aqueous layer three times with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound: Rf=0.09 (silica gel, ethyl acetate).
Workup
- temperatureWarm to ambient temperature
- customseparate the layers
- extractionextract the aqueous layer three times with ethyl acetate
- dry with materialDry the combined organic layers over Na2SO4
- filtrationfilter
- concentrationconcentrate in vacuo
- customto obtain a residue
Sources & evidence
- ORD record
- ord-cd93ba56deb84177b3d8e961da8d91b1
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06211199B1
Reaction notes
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