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 1523724노트

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HRID 1523724 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-240e4f757abf4ee3af472c74400d59d9
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079894B2

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