Cyclopentanone → Methyl 4-(N-cyclopentylamino)-3-iodobenzoate

HRID 2252737

반응식

HRID 2252737 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[I:12].[C:13]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH:13]1([NH:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=2[I:12])[CH2:17][CH2:16][CH2:15][CH2:14]1

참가 물질

7

반응물 5

HCID 8452CyclopentanoneHCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 4104649Methyl 4-amino-3-iodobenzoateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 21974264Methyl 4-(N-cyclopentylamino)-3-iodobenzoate

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A mixture of methyl 4-amino-3-iodobenzoate from above (27.69 g, 100 mmol), cyclopentanone (52.8 mL, 600 mmol), and anhydrous sodium sulfate (1000 g, 142 mmol) in 500 mL of glacial acetic acid was stirred for two hours. Solid sodium triacetoxyborohydride (76.92, 345 mmol) was added in portions and stirred for 16 hrs at room temperature. The mixture was poured on to cool 900 mL of saturated aqueous sodium bicarbonate solution carefully and extracted with 150 mL (3×) of ethyl acetate. The ethyl acetate fraction was dried and evaporated. Purification with silica gel and 0.5% ethyl acetate in hexane gave 24 g (70%).

후처리

  1. stirringstirred for 16 hrs at room temperature
  2. additionThe mixture was poured on
  3. extractionextracted with 150 mL (3×) of ethyl acetate
  4. dry with materialThe ethyl acetate fraction was dried
  5. customevaporated
  6. customPurification with silica gel and 0.5% ethyl acetate in hexane
  7. customgave 24 g (70%)

출처 및 근거

ORD 기록
ord-b394d7f4bed44f259775bb744022cfa9
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07323470B2

연결된 노트

불러오는 중…