1-(Phenylmethyl)-2,5-pyrrolidinedione → HCID 58504592, 화합물

HRID 2367229

반응식

HRID 2367229 반응식
[C:1]1([CH2:7][N:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:15]1([Mg]Br)[CH2:17][CH2:16]1>C1COCC1>[CH:15]1([C:12]2([OH:13])[N:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:9](=[O:14])[CH2:10][CH2:11]2)[CH2:17][CH2:16]1

참가 물질

4

반응물 2

HCID 952411-(Phenylmethyl)-2,5-pyrrolidinedioneHCID 178418630HCID 178418630, 화합물

생성물 1

HCID 58504592HCID 58504592, 화합물수율 33%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To 1-(phenylmethyl)-2,5-pyrrolidinedione (1 g, 5.29 mmol) in THF (50 mL) at −78° C. was added cyclopropylmagnesium bromide (42.3 mL, 21.1 mmol) dropwise. The reaction mixture was allowed to warm to 0° C. and stirred for an additional 2 hours. The reaction was quenched with a saturated aqueous solution of ammonium chloride and transferred to a separatory funnel. EtOAc was added, and the organic phase was separated. The aqueous layer was further extracted with EtOAc, and the combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% hexanes to 80% EtOAc/hexanes) afforded the title compound (400 mg, 33%) as a yellow solid. LC-MS (ES) m/z=232 [M+H]+.

후처리

  1. customThe reaction was quenched with a saturated aqueous solution of ammonium chloride
  2. customtransferred to a separatory funnel
  3. additionEtOAc was added
  4. customthe organic phase was separated
  5. extractionThe aqueous layer was further extracted with EtOAc
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ae820360a90240069134d3d173d5b4f2
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697685B2

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