Sodium hydride → HCID 71060151, compound

HRID 1036727Notes

Reaction equation

HRID 1036727 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[CH:5]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:4][NH:3]1.[H-].[Na+].ClC(Cl)(Cl)S(O[CH2:33][C:34]([F:37])([F:36])[F:35])(=O)=O>C1COCC1>[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[CH:5]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:4][N:3]1[CH2:33][C:34]([F:37])([F:36])[F:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 900272,2,2-Trifluoroethyl trichloromethanesulphonateHCID 71060285HCID 71060285, compound

Product 1

HCID 71060151HCID 71060151, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Tert-butyl 1-oxo-4-phenyl-2,7-diazaspiro[4.5]decane-7-carboxylate (1 g, 3.03 mmol) in THF (13 ml) cooled to 0° C. was treated with sodium hydride (60% in oil) (4.54 mmol, 0.182 g). The reaction mixture was stirred at 0° C. for 5 minutes and stirred at room temperature for 1 hour. The reaction mixture was cooled back down to 0° C. and treated dropwise with 1,1,1-trifluoroethyl trichloromethanesulfonate (0.547 ml, 3.33 mmol) in THF (2 ml). The reaction mixture was stirred at room temperature for 9 hours. The reaction was quenched with water and extracted with EtOAc. The organic portion was dried (MgSO4) and concentrated in vacuo. The crude product was purified by silica chromatography, eluting with 0-20% ethyl acetate/iso-hexane. The relevant fractions were combined and concentrated in vacuo to give tert-butyl 1-oxo-4-phenyl-2-(2,2,2-trifluoroethyl)-2,7-diazaspiro[4.5]decane-7-carboxylate.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. temperatureThe reaction mixture was cooled back down to 0° C.
  3. stirringThe reaction mixture was stirred at room temperature for 9 hours
  4. customThe reaction was quenched with water
  5. extractionextracted with EtOAc
  6. dry with materialThe organic portion was dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica chromatography
  9. washeluting with 0-20% ethyl acetate/iso-hexane
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7ff3a62ebeda49e5873758feab23997c
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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