Potassium Hydroxide → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 1294578Notes

Reaction equation

HRID 1294578 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[CH3:16][S+](C)(C)=O.[OH-].[K+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([O:14][CH2:16]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylateYield 90.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 44.9 g (0.225 mol) of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (31) in 500 ml acetonitrile was added successively 59.5 g (0.27 mol) trimethyl sulphoxonium iodide and 18.9 g (0.338 mol) fine crushed potassium hydroxide. The reaction mixture was vigorously stirred for two days under a nitrogen atmosphere at room temperature. After complete conversion the solvent was evaporated in vacuo and the residue was taken up in dichloromethane. The organic layer was washed with aqueous citric acid solution (6×), dried over sodium sulphate and concentrated in vacuo. This crude product was used without further purification for the next step (43.5 g, 0.204 mol, 90.6% yield).

Workup

  1. customAfter complete conversion the solvent was evaporated in vacuo
  2. washThe organic layer was washed with aqueous citric acid solution (6×)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThis crude product was used without further purification for the next step (43.5 g, 0.204 mol, 90.6% yield)

Sources & evidence

ORD record
ord-85c0d22d81dd4e1789b52b21920781cb
Source dataset
uspto-grants-2007_07
Patent number
US07241770B2

Reaction notes

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