Sodium Hydroxide → 2-Methyl-4-phenyl-8-(phenylmethyl)-2,8-diazaspiro[4.5]decane

HRID 1018636Notes

Reaction equation

HRID 1018636 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:32][CH2:31][C:17]2([C:21](=O)[N:20]([CH3:23])[C:19](=O)[CH:18]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>O>[CH2:7]([N:14]1[CH2:32][CH2:31][C:17]2([CH2:21][N:20]([CH3:23])[CH2:19][CH:18]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12709713HCID 12709713, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 127097252-Methyl-4-phenyl-8-(phenylmethyl)-2,8-diazaspiro[4.5]decaneYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Lithium aluminium hydride (1.39 g, 37 mmol) was dissolved in tetarhydrofuran (20 mL) and the intermediate (rac)-8-benzyl-2-methyl-4-phenyl-2,8-diaza-spiro[4.5]decane-1,3-dion (2.55 g, 7.32 mmol, dissolved in 20 mL dry tetrahydrofuran) was added slowly. The reaction mixture was stirred at room temperature for 2 h. Water (1.4 mL), sodium hydroxide (15% in water, 1.5 mL) and water (4.2 mL) were added dropwise. The precipitate was filtered off and the filtrate was evaporated. The residue was purified by flash chromatography (hexane/ethyl acetate/triethyl amine 30:20.1) to yield the intermediate (rac)-8-benzyl-2-methyl-4-phenyl-2,8-diaza-spiro[4.5]decane (1.40 g, 60%).

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was purified by flash chromatography (hexane/ethyl acetate/triethyl amine 30:20.1)

Sources & evidence

ORD record
ord-57402da9c0c94c3fa2260f37a54c9588
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

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