Benzyl Chloride → HCID 67166125, compound

HRID 552348Notes

Reaction equation

HRID 552348 reaction equation
[H-].[Na+].[CH2:3]([C@@H:10]1[NH:14][C:13]2([CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)[NH:12][C:11]1=[O:27])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[NH4+].[Cl-]>C1COCC1>[C:23]([O:22][C:20]([N:17]1[CH2:16][CH2:15][C:13]2([N:12]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:11](=[O:27])[C@H:10]([CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:14]2)[CH2:19][CH2:18]1)=[O:21])([CH3:24])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 7503Benzyl Chloride2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 67166196HCID 67166196, compound

Product 1

HCID 67166125HCID 67166125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

NaH (1.26 g, 52.5 mmol) was added at RT to a solution of tert-butyl 3-(S)-benzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate (12.1 g, 35 mmol) in THF (250 ml). After stirring for 1 h at 0° C., benzyl chloride (4.9 g, 38.5 mmol) was added dropwise, and the mixture was allowed to warm to RT and heated for 60 h under reflux. Subsequently, benzyl chloride (2.4 g, 19 mmol) was again added and the mixture was heated under reflux for a further 16 h. The reaction mixture was treated with aqueous saturated NH4Cl solution (20 ml) and extracted with EA (3×50 ml). The combined organic phase was dried over Na2SO4, filtered and the solvent was distilled off. Workup was carried out by means of column chromatography and afforded tert-butyl-1,3-(S)-dibenzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate in a yield of 13.5 g (88%).

Workup

  1. temperatureto warm to RT
  2. temperatureheated for 60 h
  3. temperatureunder reflux
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for a further 16 h
  6. extractionextracted with EA (3×50 ml)
  7. dry with materialThe combined organic phase was dried over Na2SO4
  8. filtrationfiltered
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-43c1098d47624f1087f82487fd13bbfe
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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