HCID 18321616, compound → HCID 68565701, compound

HRID 1867590Notes

Reaction equation

HRID 1867590 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([CH:14]1[NH:18][C:17](=[O:19])[N:16]([CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:22][CH2:21]2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([CH:14]1[CH2:15][N:16]([CH:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:22][CH2:21]2)[C:17](=[O:19])[NH:18]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 18321616HCID 18321616, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 68565701HCID 68565701, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (3.96 mL, 3.96 mmol, 1 M) was added to a solution of 5-benzyl-3-(1-benzylpiperidin-4-yl)imidazolidine-2,4-dione (120 mg, 0.330 mmol) in tetrahydrofuran (15 mL) at 0° C. and then warmed to ambient temperature. After 16 h, the reaction was quenched with water (0.150 mL), a 15% sodium hydroxide solution (0.150 mL), and water (0.450 mL). The mixture was filtered, washed with tetrahydrofuran, and concentrated. Purification by column chromatography (silica gel, 1 to 12% {1% ammonium hydroxide/methanol} in methylene chloride gradient elution), gave the title compound (30 mg). MS 350.3 (M+1)

Workup

  1. customthe reaction was quenched with water (0.150 mL)
  2. filtrationThe mixture was filtered
  3. washwashed with tetrahydrofuran
  4. concentrationconcentrated
  5. customPurification
  6. washby column chromatography (silica gel, 1 to 12% {1% ammonium hydroxide/methanol} in methylene chloride gradient elution)

Sources & evidence

ORD record
ord-29a6dd5e5cd3437995fecd5ce930a2b5
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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