Hydrochloric Acid → 2-Azaspiro[4.5]decan-8-one

HRID 1477953Notes

Reaction equation

HRID 1477953 reaction equation
O1[C:5]2([CH2:14][CH2:13][C:8]3([CH2:12][CH2:11][NH:10][CH2:9]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>CO>[CH2:9]1[C:8]2([CH2:13][CH2:14][C:5](=[O:4])[CH2:6][CH2:7]2)[CH2:12][CH2:11][NH:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 826579751,4-Dioxa-10-azadispiro[4.2.4.2]tetradecane

Product 1

HCID 686527332-Azaspiro[4.5]decan-8-oneYield 128.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecane (10 g, 50.69 mmol) in MeOH (100 mL) was added HCl aqueous solution (2 M, 30 mL, 60 mmol). The reaction mixture was stirred at rt overnight and concentrated in vacuo. The residue was dissolved in water (100 mL) and adjusted to pH=10 with a saturated Na2CO3 aqueous solution, then extracted with DCM (200 mL×3). The combined organic phases were washed with brine (200 mL), dried over anhydrous Na2SO4, then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/7) to give the title compound as a yellow solid (10 g, 100%).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in water (100 mL)
  3. extractionextracted with DCM (200 mL×3)
  4. washThe combined organic phases were washed with brine (200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/7)

Sources & evidence

ORD record
ord-49b5a6eec9fa4fb7bf947155f6757303
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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