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

HRID 734225ノート

反応式

HRID 734225 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 223413358-Azaspiro[4.5]dec-2-ene収率 99.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

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)+.

後処理

  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))

出典と根拠

ORDレコード
ord-f1ad9c64806940ac9c9207dcecffc0b4
出典データセット
uspto-grants-2009_09
特許番号
US07592334B2

反応ノート

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