Water → 3-Benzyl-8-(tert-butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one

HRID 895615Notes

Reaction equation

HRID 895615 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:24][CH2:23][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][NH:13][C:12]2=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C)C=O>[CH2:27]([N:13]1[C:12](=[O:22])[C:11]2([CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:24][CH2:23]2)[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 389488tert-Butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

Product 1

HCID 223806103-Benzyl-8-(tert-butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-oneYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-(tert-Butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one (1.441 g) was dissolved in N,N-dimethylformamide (28 ml), added with sodium hydride (60%, in oil, 521 mg) and stirred at room temperature for 1.5 hours. The reaction mixture was added with benzyl bromide (1.81 ml) with ice cooling and further stirred at room temperature for 1 hour. The reaction mixture was added with water (50 ml) and extracted twice with dichloromethane (70 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=5:1 →4:1) to obtain 1.710 g of the title compound. Yield: 94%.

Workup

  1. stirringfurther stirred at room temperature for 1 hour
  2. extractionextracted twice with dichloromethane (70 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=5:1 →4:1)

Sources & evidence

ORD record
ord-ca092fd3c4da49648df8cd71fa6ea110
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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