1-(Phenylmethyl)-2,5-pyrrolidinedione → HCID 58504592、化合物

HRID 2367229

反応式

HRID 2367229 の反応式
[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

参加物

4

反応物 2

HCID 952411-(Phenylmethyl)-2,5-pyrrolidinedioneHCID 178418630HCID 178418630、化合物

生成物 1

HCID 58504592HCID 58504592、化合物収率 33%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-ae820360a90240069134d3d173d5b4f2
出典データセット
uspto-grants-2014_04
特許番号
US08697685B2

関連ノート

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