HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-Benzyl-8-(tert-butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzyl Bromide | HCID 7498 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | tert-Butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate | HCID 389488 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-Benzyl-8-(tert-butoxycarbonyl)-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one | HCID 22380610 | 94% |
Reaction Steps
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%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06916822B2 |
| Source dataset | uspto-grants-2005_07 |
| ORD ID | ord-ca092fd3c4da49648df8cd71fa6ea110 |
| Source note | uspto-grants-2005_07 |