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

HRID 734225노트

반응식

HRID 734225 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

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)+.

후처리

  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))

출처 및 근거

ORD 기록
ord-f1ad9c64806940ac9c9207dcecffc0b4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592334B2

반응 노트

불러오는 중…