Acetic Anhydride → 1-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-acetoxyethyl)pyrrolidine

HRID 2230506Notes

Reaction equation

HRID 2230506 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)([CH2:13][CH2:14][OH:15])[CH2:9]1)=[O:7].ClCCl.N1C=CC=CC=1.[C:40](OC(=O)C)(=[O:42])[CH3:41]>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)([CH2:13][CH2:14][O:15][C:40](=[O:42])[CH3:41])[CH2:9]1)=[O:7]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 184644171-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidineHCID 21875418Pyridine methylene chloride

Product 1

HCID 184645531-(3,4,5-Trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-acetoxyethyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

Combine 1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-hydroxyethyl)pyrrolidine (4.5 g, 9.9 mmol) and dichloromethane/pyridine (70 mL, 6/1). Add acetic anhydride (1.04 mL, 11.0 mmol) and 4-dimethylaminopyridine (50 mg, 0.41 mmol). After 2 hours, concentrate the reaction mixture in vacuo to obtain a residue. Dissolve the residue in ethyl acetate and extract with 1M hydrochloric acid solution (2×200 mL), saturated sodium bicarbonate solution, and saturated sodium chloride solution. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give 1-(3,4,5-trimethoxybenzoyl)-3-(3,4-dichlorophenyl)-3-(2-acetoxyethyl)pyrrolidine: Rf=0.38 (silica gel, ethyl acetate). Elemental Analysis calculated for C24H27Cl2NO6: C 58.07; H 5.48; N 2.82; Found: C, 57.67; H, 5.46; N, 2.84.

Workup

  1. concentrationconcentrate the reaction mixture in vacuo
  2. customto obtain a residue
  3. extractionextract with 1M hydrochloric acid solution (2×200 mL), saturated sodium bicarbonate solution, and saturated sodium chloride solution
  4. dry with materialDry the organic layer over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue

Sources & evidence

ORD record
ord-a4f90952dde54a1cabdd925e43d738ae
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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