Ethyl Acetate → 1-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-hydroxypropyl)-2-oxopyrrolidine

HRID 323279Notes

Reaction equation

HRID 323279 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)([CH2:12][CH2:13][CH2:14][O:15][Si](C(C)(C)C)(C)C)[C:8]1=[O:31].[F-].[NH4+].C(OCC)(=O)C>CO.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[CH2:6][N:7]1[CH2:11][CH2:10][C:9]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)([CH2:12][CH2:13][CH2:14][OH:15])[C:8]1=[O:31]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25516Ammonium fluorideHCID 184646181-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-t-butyldimethylsilyloxypropyl)-2-oxopyrrolidine

Product 1

HCID 184644801-(3,4,5-Trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-hydroxypropyl)-2-oxopyrrolidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Combine 1-(3,4,5-trimethoxybenzyl)-3-(4-fluorophenylmethyl)-3-(3-(t-butyldimethylsilyloxy)propyl)-2-oxopyrrolidine (1.08 mmol) and ammonium fluoride (0.24 g, 6.48 mmol) in methanol (10 mL). Heat to reflux. After 2 hours, cool to ambient temperature and pour the reaction mixture into a brine (30 mL). Extract five times with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give the title compound: Rf=0.30 (silica gel, ethyl acetate).

Workup

  1. temperatureHeat to reflux
  2. extractionExtract five times with dichloromethane
  3. dry with materialDry the combined organic layers over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-166e06bff43a48dfb0d011d8c5c30126
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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