Sodium Iodide → 9-[(cyclopentyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one

HRID 567369노트

반응식

HRID 567369 반응식
[C:1]([C:5]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:6]=1[C:7]1[C:8](=[O:18])[CH2:9][CH2:10][CH2:11][C:12]=1[NH:13]2)([O:3][CH3:4])=[O:2].C([O-])([O-])=O.[K+].[K+].[CH:25]1([CH2:30]Cl)[CH2:29][CH2:28][CH2:27][CH2:26]1.[Na+].[I-].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Na+].[I-].O>[CH:25]1([CH2:30][N:13]2[C:12]3[CH2:11][CH2:10][CH2:9][C:8](=[O:18])[C:7]=3[C:6]3[C:14]2=[CH:15][CH:16]=[CH:17][C:5]=3[C:1]([O:3][CH3:4])=[O:2])[CH2:29][CH2:28][CH2:27][CH2:26]1

참가 물질

9

반응물 5

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 11368514methyl 4-oxo-2,3,4,9-tetrahydro-1H-carbazole-5-carboxylateHCID 12815409(Chloromethyl)cyclopentane4회

생성물 1

HCID 227386049-[(cyclopentyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one수율 71%

시약·촉매·용매 3

HCID 5238Sodium Iodide촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A suspension of 5-carbomethoxy-1,2-dihydro-9H-carbazol-4(3H)-one (820 g, 3.37 mmol), a catalytic amount of NaI (ca. 10 mg) and K2CO3 (930 mg, 6.74 mmol) in 6 mL of DMF was treated with cyclopentylmethyl chloride (JOC, 1964, 29, 421-423; 400 mg, 3.37 mmol). After stirring overnight at ambient temperature, an additional 800 mg of cyclopentylmethyl chloride and 1 g of NaI were added, and the resulting mixture was heated at 80° C. overnight. An additional 800 mg of cyclopentylmethyl chloride and 2.2 g of Cs2CO3 were added, and the reaction mixture was heated at 80° C. for 24 h. An additional 1.6 g of cyclopentylmethyl chloride was added, and the reaction mixture was heated at 80° C. for 3 d The mixture was poured into H2O (30 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by radial chromatography on silica gel (elution with gradient of 10% to 40% EtOAc/hexanes) to afford 775 mg (2.38 mmol; 71%) of 9-[(cyclopentyl)methyl]-5-carbomethoxy-1,2-dihydrocarbazol-4(3H)-one as a brown foam. MS (ES) m/e 326 (M+1), 384 (M+AcO−).

후처리

  1. temperaturethe resulting mixture was heated at 80° C. overnight
  2. temperaturethe reaction mixture was heated at 80° C. for 24 h
  3. temperaturethe reaction mixture was heated at 80° C. for 3 d The mixture
  4. extractionextracted with EtOAc (3×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by radial chromatography on silica gel (elution with gradient of 10% to 40% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-a83c6ae3f37e4aee96ce9ecde72e7d50
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177440B1

반응 노트

불러오는 중…