Water → HCID 57672003, compound

HRID 871991Notes

Reaction equation

HRID 871991 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:36])=[C:6]([CH:35]=1)[O:7][CH2:8][C:9]1[C:10]([C:23]2[CH:28]=[C:27]([C:29](OC)=[O:30])[CH:26]=[CH:25][C:24]=2[O:33][CH3:34])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[NH:14]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:36])=[C:6]([CH:35]=1)[O:7][CH2:8][C:9]1[C:10]([C:23]2[CH:28]=[C:27]([CH2:29][OH:30])[CH:26]=[CH:25][C:24]=2[O:33][CH3:34])=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]([CH3:19])[C:16](=[O:20])[C:15]([CH3:22])([CH3:21])[NH:14]2

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl Acetate2×HCID 21226445Aluminium lithium hydrideHCID 57671881HCID 57671881, compound

Product 1

HCID 57672003HCID 57672003, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8-(5-Fluoro-2-methylphenoxymethyl)-7-(2-methoxy-5-methoxycarbonylphenyl)-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Compound No. 6-37, 50.2 mg, 0.102 mmol) was dissolved in anhydrous tetrahydrofuran (0.5 ml), and lithium aluminum hydride (6.8 mg, 0.18 mmol) was added thereto at 0° C. After the reaction mixture was stirred at same temperature for 30 minutes, ethyl acetate (1 mL) and water (1 mL) were added thereto successively. Moreover ethyl acetate (10 mL) and water (10 mL) were added and partitioned. The organic layer was washed with saturated brine (10 mL), dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (29.8 mg) as a pale yellow solid. (Yield 47%)

Workup

  1. customat 0° C
  2. custompartitioned
  3. washThe organic layer was washed with saturated brine (10 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-abc074b6838348959b91fd7dfd2164fc
Source dataset
uspto-grants-2015_03
Patent number
US08975256B2

Reaction notes

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