Sodium Carbonate → 1-(2,4,5-Trimethoxybenzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 323342Notes

Reaction equation

HRID 323342 reaction equation
[C:1]1([C:7]2([CH2:12][CH2:13][OH:14])[CH2:11][CH2:10][NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:21][O:22][C:23]1[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[CH:28][C:24]=1[C:25](Cl)=[O:26].C(OCC)(=O)C.C(O)C>C(OCC)(=O)C.O.C(OCC)(=O)C>[CH3:21][O:22][C:23]1[CH:31]=[C:30]([O:32][CH3:33])[C:29]([O:34][CH3:35])=[CH:28][C:24]=1[C:25]([N:9]1[CH2:10][CH2:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([CH2:12][CH2:13][OH:14])[CH2:8]1)=[O:26]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 27608092,4,5-Trimethoxybenzoyl chlorideHCID 184645642-(3-Phenylpyrrolidin-3-yl)ethanolHCID 21584252Ethanol ethylacetate

Product 1

HCID 184648671-(2,4,5-Trimethoxybenzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 22728543Water ethylacetateSolvent

Procedure

Combine 3-phenyl-3-(2-hydroxyethyl)pyrrolidine (1.8 mmol) and sodium carbonate (0.76 g, 7.2 mmol) in ethyl acetate/water (10 mL/10 mL). With stirring, add a solution of 2,4,5-trimethoxybenzoyl chloride (1.1 g, 1.8 mmol) in ethyl acetate (1 mL). After 18 hours, separate the layers and extract the aqueous layer twice with ethyl acetate. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 9/1 ethyl acetate/ethanol to give the title compound.

Workup

  1. customseparate the layers
  2. extractionextract the aqueous layer twice with ethyl acetate
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-aa360c8fa2a5439d806f2f4ba8a49f94
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

Loading…