8-Azaspiro[4.5]dec-2-ene-7,9-dione → 8-Azaspiro[4.5]dec-2-ene

HRID 734225Notes

Reaction equation

HRID 734225 reaction equation
[CH2:1]1[C:5]2([CH2:10][C:9](=O)[NH:8][C:7](=O)[CH2:6]2)[CH2:4][CH:3]=[CH:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:4]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:1][CH:2]=[CH:3]1

Participants

4

Reactant 2

HCID 150680348-Azaspiro[4.5]dec-2-ene-7,9-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 223413358-Azaspiro[4.5]dec-2-eneYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 8-azaspiro[4.5]dec-2-ene-7,9-dione (3.3 g, 20 mmol) [prepared according to Cipollina, J. A.; et. al. J. Med. Chem. 1991, 34, 3316.] in THF (200 mL) at 0° C. was added LAH (3.42 mg, 90 mmol) portion-wise. After 1 h at 0° C., the solution warmed to 25° C. and was then heated to 60° C. After an additional 1 h at reflux, the solution was cooled and quenched by dropwise addition of a saturated solution of Rochelle's salt. The aqueous phase was extracted several times with DCM and the combined organic fractions were dried (Na2SO4), concentrated and purified via column chromatography (silica, 3% MeOH in DCM (1% NH4OH)) yielding the title compound (2.74 g, quant.) as a yellow oil: LCMS (ES) m/e 160 (M+Na)+.

Workup

  1. temperaturewas then heated to 60° C
  2. temperatureAfter an additional 1 h at reflux
  3. temperaturethe solution was cooled
  4. customquenched by dropwise addition of a saturated solution of Rochelle's salt
  5. extractionThe aqueous phase was extracted several times with DCM
  6. dry with materialthe combined organic fractions were dried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified via column chromatography (silica, 3% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-f1ad9c64806940ac9c9207dcecffc0b4
Source dataset
uspto-grants-2009_09
Patent number
US07592334B2

Reaction notes

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