Potassium Carbonate → 12-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo-[3,4-c]carbazole

HRID 1418639

反応式

HRID 1418639 の反応式
[C:1]([CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[NH:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[C:14]3[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:13]=3[C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)#N.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[CH3:57][C:58]1([CH3:75])[O:62]C(COS(C2C=CC(C)=CC=2)(=O)=O)C[O:59]1.C(OC(C)C)(C)C.CC(C)=O>C1(C)C=CC=CC=1>[CH3:57][C:58]1([CH3:75])[O:62][CH:3]([CH2:4][N:5]2[C:17]3[C:16]4[NH:18][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=5[C:15]=4[C:14]4[C:25](=[O:30])[N:26]([CH3:29])[C:27](=[O:28])[C:13]=4[C:12]=3[C:11]3[C:6]2=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:1][O:59]1

参加物

8

反応物 6

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 2350972,2-Dimethyl-1,3-dioxolan-4-ylmethyl p-toluenesulfonateHCID 2121684212-(2-Cyanoethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazoleHCID 22221350Acetone diisopropyl ether

生成物 1

HCID 2121686012-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo-[3,4-c]carbazole

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

12-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo-[2,3-a]pyrrolo[3,4-c]carbazole is prepared in the following manner: 3g (8.84 mmol) 6,7,12,13-Tetrahydro-6-methyl-5,1-dioxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole (precursor for Example 5) are stirred for 2 hours at 20° C. with 595 mg (9 mmol) powdered potassium hydroxide, 620 mg (4.5 mmol) potassium carbonate and 300 mg (1.1 mmol) 18-crown-6 in 200 ml toluene under an atmosphere of nitrogen. Subsequently, 2.6 g (9 mmol) 2,2-dimethyl-4-(4-methylphenylsulphonyloxymethyl)-1,3-dioxolan (see Biochemistry, 1971, 10, 3204) are added thereto and the reaction mixture is heated under reflux for 16 hours. After cooling, the reaction mixture is evaporated in a vacuum and the residue is taken up in ethyl acetate and water. The ethyl acetate solution is separated off, washed with water, dried over anhydrous sodium sulphate, filtered and evaporated. The residue is chromatographed on silica gel with toluene/acetone (9:1 v/v), the fraction with the Rf 0.65 in toluene/acetone (3:1 v/v) is isolated, stirred with 20 ml diisopropyl ether/acetone (4:1 v/v) and the yellow crystals formed of 12-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo[2,3-a]pyrrolo-[3,4-c]carbazole filtered off.

後処理

  1. custom12-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-6,7,12,13-tetrahydro-6-methyl-5,7-dioxo-5H-indolo-[2,3-a]pyrrolo[3,4-c]carbazole is prepared in the following manner
  2. temperaturethe reaction mixture is heated
  3. temperatureunder reflux for 16 hours
  4. temperatureAfter cooling
  5. customthe reaction mixture is evaporated in a vacuum
  6. customThe ethyl acetate solution is separated off
  7. washwashed with water
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue is chromatographed on silica gel with toluene/acetone (9:1 v/v)
  12. customthe fraction with the Rf 0.65 in toluene/acetone (3:1 v/v) is isolated

出典と根拠

ORDレコード
ord-1cd041c7f0dd4394ad0ad5ba3f1103cd
出典データセット
uspto-grants-1999_03
特許番号
US05883114

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