Hydrochloric Acid → HCID 19390113, compound

HRID 1757165Notes

Reaction equation

HRID 1757165 reaction equation
[F:1][C:2]1[C:3]([O:37][CH3:38])=[C:4]([CH:33]=[C:34]([F:36])[CH:35]=1)[CH2:5][CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:9][N:8]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)[C:7]1=O.Cl>C1COCC1>[F:1][C:2]1[C:3]([O:37][CH3:38])=[C:4]([CH:33]=[C:34]([F:36])[CH:35]=1)[CH2:5][CH:6]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH2:9][N:8]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19390116HCID 19390116, compound

Product 1

HCID 19390113HCID 19390113, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

200 ml of a solution of 17.78 g (33.8 mmol) of 3-(3,5-difluoro-2-methoxybenzyl)-N-(3,4-dimethoxybenzyl)-4-(3,4-dimethoxyphenyl)pyrrolidone in THF was dropwise added at 0° C. in a nitrogen atmosphere to 150 ml of a 1M solution of a borane/THF complex in THF. The mixture was heated under reflux for 2 hr and cooled, and 50 ml of a 6N hydrochloric acid solution was added thereto. The mixture was heated to 60° C. After stirring for 2 hr, THF was concentrated in vacuo and extracted twice with methylene chloride. The obtained organic phase was washed with a saline solution and dried over anhydrous sodium sulfate, and the solvent was distilled off in vacuo. The residue was subjected to silica gel column chromatography (ethyl acetate:n-hexane=4:1) to prepare 12.46 g (yield: 72%) of the intended product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. temperaturecooled
  4. concentrationTHF was concentrated in vacuo
  5. extractionextracted twice with methylene chloride
  6. washThe obtained organic phase was washed with a saline solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-dfa57b3af74740dfac391cc77feaedfc
Source dataset
uspto-grants-1995_08
Patent number
US05444083

Reaction notes

Loading…