Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate → Ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate

HRID 1523724ノート

反応式

HRID 1523724 の反応式
[CH2:1]([N:8]1[C:13](=O)[CH:12]2[CH:10]([CH:11]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 15713436Ethyl 3-benzyl-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate

生成物 1

HCID 15818457Ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate収率 62.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of ethyl 3-benzyl-2,4-dioxo-3-aza bicyclo[3.1.0]hexane-6-carboxylate (SYNLETT, 1996, 1097; 5.0 grams, 18.3 mmol) in tetrahydrofuran (74 mL) cooled at 0° C., BH3-DMS (2N solution in tetrahydrofuran 36 mL, 73.2 mmol) was added over a period of 30 minutes. The reaction temperature was gradually raised to reflux for 6 hours. After cooling the reaction mixture to 0° C., it was quenched by adding aqueous ammonium chloride solution and was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography to obtain ethyl 3-benzyl-3-aza bicyclo[3.1.0]hexane-6-carboxylate (2.8 grams)

後処理

  1. temperatureThe reaction temperature was gradually raised
  2. temperatureto reflux for 6 hours
  3. customit was quenched
  4. additionby adding aqueous ammonium chloride solution
  5. extractionwas extracted with ethyl acetate
  6. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-240e4f757abf4ee3af472c74400d59d9
出典データセット
uspto-grants-2015_07
特許番号
US09079894B2

反応ノート

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