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Di-tert-butyl dicarbonate → 1-t-Butoxycarbonyl-2,3-dihydro-7-methyl-6-nitroindole

HRID 1275649
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HRID 1275649 반응식
[CH3:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2.[CH3:14][C:15]1[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]2[C:23]=1[NH:22][CH2:21][CH2:20]2.[C:27]([O:31][C:32](O[C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:33])([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:31][C:32]([N:22]1[C:23]2[C:19](=[C:18]([N+:24]([O-:26])=[O:25])[CH:17]=[CH:16][C:15]=2[CH3:14])[CH2:20][CH2:21]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].[C:38]([O:37][C:35]([N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([N+:11]([O-:13])=[O:12])[C:2]=2[CH3:1])[CH2:7][CH2:8]1)=[O:36])([CH3:39])([CH3:40])[CH3:41]
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참가 물질

6

반응물 3

HCID 90495Di-tert-butyl dicarbonateHCID 158963682,3-Dihydro-7-methyl-6-nitroindoleHCID 158963697-Methyl-4-nitro-indoline

생성물 2

HCID 158963701-t-Butoxycarbonyl-2,3-dihydro-7-methyl-6-nitroindoleHCID 158963761h-Indole-1-carboxylic acid,2,3-dihydro-7-methyl-4-nitro-,1,1-dimethylethyl ester

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

The isomeric mixture of 2,3-dihydro-7-methyl-6-nitroindole and 2,3-dihydro-7-methyl-4-nitroindole (6.10 g; 0.0337 mol) is dissolved in methylene chloride (50 mL). To this solution is added N,N-dimethylaminopyridine (4.30 g; 0.0337 mol) and di-t-butyidicarbonate (22.5 g; 0.101 mol). Additional methylene chloride (50 mL) is added and the flask is equipped with a reflux condenser. The solution is allowed to stir overnight under an atmosphere of argon. The methylene chloride solution is extracted with four 100-mL portions of aqueous citric acid and is dried over anhydrous potassium carbonate. The solution is filtered, concentrated by rotary evaporation and dried under vacuum to give an oily, brown solid. The crude mixture is purified by silica gel flash column chromatography using 5% ethyl acetate/hexanes as eluent to give 2.44 g of 1-t-butoxycarbonyl-2,3-dihydro-7-methyl-4-nitroindole as a yellow solid and 2.6 g of 1-t-butoxycarbonyl-2,3-dihydro-7-methyl-6-nitroindole as well as some unseparated material.

후처리

  1. customthe flask is equipped with a reflux condenser
  2. extractionThe methylene chloride solution is extracted with four 100-mL portions of aqueous citric acid
  3. dry with materialis dried over anhydrous potassium carbonate
  4. filtrationThe solution is filtered
  5. concentrationconcentrated by rotary evaporation
  6. customdried under vacuum
  7. customto give an oily, brown solid
  8. customThe crude mixture is purified by silica gel flash column chromatography

출처 및 근거

ORD 기록
ord-d39ff4cd35254c3b884f15d6cf2304e7
출처 데이터셋
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06162818

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