Sodium hydride → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 1896009Notes

Reaction equation

HRID 1896009 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[C:9]([N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>CN(C=O)C>[O:22]1[C:19]2([CH2:20][CH2:21][N:16]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:17][CH2:18]2)[CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 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 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Trimethylsulfoxonium iodide (580 mg, 2.64 mmol) was added to a suspension of NaH (106 mg, 2.64 mmol) at 0° C. under nitrogen atmosphere. After 15 min. under stirring at the same temperature, N-Boc-4-piperidone (500 mg, 2.51 mmol) dissolved in DMF (5 mL) was added. Stirring was continued and, after 2 h at r.t., the reaction mixture was quenched with water and EtOAc. The combined extracts were washed, dried over Na2SO4 and evaporated to dryness. The crude residue was purified by flash chromatography (EtOAc—Petroleum Ether 9:1) affording the title product (380 mg).

Workup

  1. additionwas added
  2. customthe reaction mixture was quenched with water and EtOAc
  3. washThe combined extracts were washed
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude residue was purified by flash chromatography (EtOAc—Petroleum Ether 9:1)

Sources & evidence

ORD record
ord-a947b199d8da4d158bde641bec2413e9
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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