Sulfoxonium, trimethyl-, iodide (1:1) → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 1827237Notes

Reaction equation

HRID 1827237 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[I-].[CH3:16][S+](C)(C)=O.CC(C)([O-])C.[Na+]>C1COCC1.CN(C=O)C>[O:1]1[C:2]2([CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH2:16]1

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 23676156Sodium t-butoxide

Product 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (0.50 g, 2.51 mmol) in THF/DMF (2:1, 6 mL) at 60° C. was added trimethylsulfoxonium iodide (0.58 g, 2.63 mmol) and sodium t-butoxide (0.25 g, 2.63 mmol). The reaction mixture was stirred at 60° C. for 30 min, cooled to RT and concentrated. Water was added and the mixture was extract with EtOAc twice. The combined organics were dried over Na2SO4, filtered and concentrated. Purification on silica gel (3:1, hexanes:EtOAc) gave tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate as a clear oil that solidified upon standing.

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated
  3. additionWater was added
  4. extractionthe mixture was extract with EtOAc twice
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification on silica gel (3:1, hexanes:EtOAc)

Sources & evidence

ORD record
ord-b6239d9b7de74b6784b31c26b1f5bfad
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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