Water → HCID 10181711, compound

HRID 1272288Notes

Reaction equation

HRID 1272288 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:11][C:12]1([CH3:45])[C@H:16]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[C:15]2[C:24]([CH3:44])=[C:25]([N:30]3[C:35](=O)[CH2:34][CH:33]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH2:32][C:31]3=O)[C:26]([CH3:29])=[C:27]([CH3:28])[C:14]=2[O:13]1.O>C1COCC1>[CH3:11][C:12]1([CH3:45])[C@H:16]([C:17]2[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[C:15]2[C:24]([CH3:44])=[C:25]([N:30]3[CH2:35][CH2:34][CH:33]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH2:32][CH2:31]3)[C:26]([CH3:29])=[C:27]([CH3:28])[C:14]=2[O:13]1

Participants

6

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) Chloride2×HCID 10115947HCID 10115947, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10181711HCID 10181711, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Aluminum chloride (913 mg, 6.9 mmol) was added to THF (10 mL) under ice cooling, and allowed to warm to room temperature so as to dissolve the aluminum chloride. The mixture was cooled with ice cooling and then lithium aluminium hydride (260 mg, 6.9 mmol) was added. After stirring for 15 minutes, A solution of (3R)-1-(2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-yl)-4-phenylpiperidine-2,6-dione obtained in Example 23 (640 mg, 1.4 mmol) in THF (5 ml) was added to the mixture under ice cooling. After the mixture was refluxed for 2 hours, the resulting mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=25/1) to obtain 350 mg (yield 58%) of the title compound via recrystallization (hexane). mp. 137–140° C.

Workup

  1. temperatureThe mixture was cooled with ice cooling
  2. temperatureAfter the mixture was refluxed for 2 hours
  3. temperaturethe resulting mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=25/1)

Sources & evidence

ORD record
ord-bda693e67f3d4eba86b52bb3444cd1ce
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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