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Trimethylaluminum → 5-(2-Dimethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carboxylic acid tert-butyl ester

HRID 2191441
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HRID 2191441 반응식
C([O:3][C:4]([C:6]1[C:7]([CH3:27])=[C:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])=O)C.C[Al](C)C>C1(C)C=CC=CC=1>[C:23]([O:22][C:20]([C:8]1[NH:9][C:10]2[CH2:11][CH2:12][CH2:13][N:14]([CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:4](=[O:3])[C:6]=2[C:7]=1[CH3:27])=[O:21])([CH3:26])([CH3:25])[CH3:24]
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참가 물질

4

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HCID 16682925TrimethylaluminumHCID 592500755-[3-(2-dimethylamino-ethylamino)-propyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

생성물 1

HCID 592500935-(2-Dimethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carboxylic acid tert-butyl ester수율 71.4%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

5-[3-(2-Dimethylamino-ethylamino)-propyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 23a (5.85 g, 13.8 mmol) was dissolved in 130 ml of toluene under stirring, and added slowly with a solution of trimethyl aluminum in toluene (12 ml, 2 mol/L, 24 mmol) to the solution under an argon atmosphere. Upon the completion of the addition, the reaction mixture was stirred for 10 minutes at room temperature until no white smoke was released, and heated to reflux for 3 hours in an oil bath. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was quenched with ice water. After the reaction system was naturally cooled down to room temperature, the mixture was added with hydrochloric acid solution (50 ml, 2 mol/L) and stirred for 10 minutes. The mixture was adjusted to pH 9 with aqueous sodium hydroxide solution (2 mol/L), and extracted with dichloromethane (50 ml×4). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered to remove the drying agent and concentrated under reduced pressure to obtain the title compound 5-(2-dimethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carboxylic acid tert-butyl ester 23b (3.3 g, yield 71.4%) as a yellow solid.

후처리

  1. additionUpon the completion of the addition
  2. stirringthe reaction mixture was stirred for 10 minutes at room temperature until no white smoke
  3. temperatureheated
  4. temperatureto reflux for 3 hours in an oil bath
  5. customthe reaction mixture was quenched with ice water
  6. additionthe mixture was added with hydrochloric acid solution (50 ml, 2 mol/L)
  7. stirringstirred for 10 minutes
  8. extractionextracted with dichloromethane (50 ml×4)
  9. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customto remove the drying agent
  12. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7050e123dd3a4ab790537c5483f294e4
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08329682B2

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