12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo(2,3-a)pyrrolo(3,4-c)carbazole → 12-(2-Cyanoethyl)-6,7,12,13-tetrahydro-7-hydroxy-13-methyl-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole

HRID 2395709

반응식

HRID 2395709 반응식
[C:1]([CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[N:18]([CH3:25])[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[C:14]3[C:26](=[O:29])[NH:27][CH2:28][C:13]=3[C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)#[N:2].C([O-])(=[O:32])C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[C:1]([CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[N:18]([CH3:25])[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[C:14]3[C:26](=[O:29])[NH:27][CH:28]([OH:32])[C:13]=3[C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)#[N:2]

참가 물질

4

반응물 2

HCID 350112-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo(2,3-a)pyrrolo(3,4-c)carbazoleHCID 178418268HCID 178418268, 화합물

생성물 1

HCID 1898988312-(2-Cyanoethyl)-6,7,12,13-tetrahydro-7-hydroxy-13-methyl-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

140 mg (0.37 mmole) 12-(2-cyanoethyl)-6,7,12,13-tetrahydro-13-methyl-5-oxo-5H-indolo[2,3a]pyrrolo[3,4-c]carbazole (Example 2) are stirred for 2 days at 20° C. in 20 mL glacial acetic acid with 197 mg (0.44 mole) lead tetraacetate. The solvent is evaporated in a vacuum and the residue partitioned between 50 mL tetrahydrofuran and 50 mL of saturated sodium hydrogencarbonate solution. The tetrahydrofuran phase is separated, washed with saturated sodium chloride solution, dried over anhydrous sodium sulphate and evaporated. The residue is chromatographed on silica gel with toluene/ethyl acetate 95:5 (v/v) and dichloromethan/methanol 98:2 (v/v). The fraction with an Rf of 0.1 in toluene/ethyl acetate 3:1 (v/v) is isolated. 12-(2-Cyanoethyl)-6,7,12,13-tetrahydro-7-hydroxy-13-methyl-5-oxo-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole is obtained in the form of beige crystals which decompose above about 220° C.

후처리

  1. customThe solvent is evaporated in a vacuum
  2. customthe residue partitioned between 50 mL tetrahydrofuran and 50 mL of saturated sodium hydrogencarbonate solution
  3. customThe tetrahydrofuran phase is separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. customThe residue is chromatographed on silica gel with toluene/ethyl acetate 95:5 (v/v) and dichloromethan/methanol 98:2 (v/v)
  8. customThe fraction with an Rf of 0.1 in toluene/ethyl acetate 3:1 (v/v) is isolated

출처 및 근거

ORD 기록
ord-db1bb4f7a08445c1864e8bd020234a07
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05489608

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