Lithium Hydroxide → 1-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

HRID 1682958Notes

Reaction equation

HRID 1682958 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:10][CH2:9][N:8]([C:11](=[O:24])[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)[CH2:7]1)C.[Li+].[OH-]>CO>[Cl:32][C:27]1[CH:26]=[C:25]([C:6]2([CH2:5][CH2:4][OH:3])[CH2:10][CH2:9][N:8]([C:11](=[O:24])[C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=3)[CH2:7]2)[CH:30]=[CH:29][C:28]=1[Cl:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 54420365HCID 54420365, compound

Product 1

HCID 184644171-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(+)-Ethyl-2-[3-(3,4-dichloro-phenyl)-1-(3,4,5-trimethoxy-benzoyl)-pyrrolidin-3-yl]-acetate (670 mg, 1.351 mmol, 99% ee) was dissolved in methanol (15 mL) and treated with LiOH (4.2 mL, 1N, 3.1 eq.) at ambient temperature for 3.5 h. The organics were concentrated in vacuo. The residue was dissolved in dichloromethane and washed with 1N HCl (50 mL), 5% NaHCO3 (50 mL), dried over MgSO4, filtered, and concentrated in vacuo to obtain a residue. The residue was dried under high vacuum for 18 h to give the title compound:

Workup

  1. concentrationThe organics were concentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with 1N HCl (50 mL), 5% NaHCO3 (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue
  8. customThe residue was dried under high vacuum for 18 h

Sources & evidence

ORD record
ord-36fadcb3535e43019a89c11ce82626ae
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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