Acetic Acid → Methyl 3-bromo-5-(cyclopentylamino)benzoate

HRID 2208690노트

반응식

HRID 2208690 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([Br:13])[CH:12]=1)[C:5]([O:7][CH2:8]C)=[O:6].[C:14]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Br:13][C:11]1[CH:10]=[C:4]([CH:3]=[C:2]([NH:1][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:12]=1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 63021768Ethyl 3-amino-5-bromobenzoate

생성물 1

HCID 70873691Methyl 3-bromo-5-(cyclopentylamino)benzoate수율 61.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of ethyl 3-amino-5-bromobenzoate (2 g, 8.73 mmol) and cyclopentanone (2.2 g, 26.1 mmol) in methanol (20 mL), acetic acid (1.04 g, 17.4 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (1.37 g, 21.83 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford desired compound (1.6 g, 61%).

후처리

  1. customreaction
  2. customreaction
  3. stirringstirred overnight
  4. customOn completion, solvent was removed under reduced pressure and crude material
  5. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-5d2c1e4aab074f62ba1737644f179328
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09376422B2

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