Sodium Carbonate → tert-Butyl 8-oxo-2-azaspiro[4.5]decane-2-carboxylate

HRID 1477954Notes

Reaction equation

HRID 1477954 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[CH2:4][CH2:3][NH:2]1.[C:12]([O-:15])([O-])=[O:13].[Na+].[Na+]>C1COCC1.O>[O:11]=[C:8]1[CH2:9][CH2:10][C:5]2([CH2:1][N:2]([C:12]([O:15][C:5]([CH3:6])([CH3:1])[CH3:4])=[O:13])[CH2:3][CH2:4]2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 686527332-Azaspiro[4.5]decan-8-one

Product 1

HCID 71711106tert-Butyl 8-oxo-2-azaspiro[4.5]decane-2-carboxylateYield 108.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-azaspiro[4.5]decan-8-one (10 g, 65.26 mmol) in a mixture of THF and H2O (3/1 (v/v), 200 mL) were added (Boc)20 (28.48 g, 130.53 mmol) and Na2CO3 (13.83 g, 130.53 mmol). The reaction mixture was stirred at rt for 2 h, then quenched with H2O (200 mL) and extracted with EtOAc (300 mL×3). The combined organic phases were washed with brine (500 mL), dried over Na2SO4, concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/10) to give the product as colorless oil (9 g, 54.5%).

Workup

  1. customquenched with H2O (200 mL)
  2. extractionextracted with EtOAc (300 mL×3)
  3. washThe combined organic phases were washed with brine (500 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/10)

Sources & evidence

ORD record
ord-ce7d1ec3654b4915befb8e96caf6974e
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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