Acetic Anhydride → HCID 54420365, compound

HRID 1682957Notes

Reaction equation

HRID 1682957 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2(CCO)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:31]([O:34][C:35](=O)[CH3:36])(=[O:33])[CH3:32]>ClCCl.N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:35]([O:34][C:31](=[O:33])[CH2:32][C:9]1([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH2:10]1)[CH3:36]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 184644171-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine

Product 1

HCID 54420365HCID 54420365, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21875418Pyridine methylene chlorideSolvent

Procedure

2-[3-(3,4-Dichloro-phenyl)-1-(3,4,5-trimethoxybenzoyl)-pyrrolidin-3-yl]-ethanol (4.5 g, 9.9 mmol) was dissolved in dichloromethane/pyridine (70 mL, 6/1). The solution was treated with acetic anhydride (1.04 mL, 11.02 mmol, 1.1 eq.) and 4-dimethylaminopyridine (50 mg, 0.41 mmol, 0.04 eq.). The solution was allowed to stir for 2 h at ambient temperature. The organics were concentrated in vacuo and the residue was dissolved in ethyl acetate and washed with 1N HCl (2×200 mL), 5% NaHCO3 (100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (300 g) with ethyl acetate to afford the title compound:

Workup

  1. concentrationThe organics were concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 1N HCl (2×200 mL), 5% NaHCO3 (100 mL), brine (100 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed on silica gel (300 g) with ethyl acetate

Sources & evidence

ORD record
ord-2d3f4e01c10f43b6ba32f6d5c038720b
Source dataset
uspto-grants-1997_06
Patent number
US05635510

Reaction notes

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