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

HRID 2191399Notes

Reaction equation

HRID 2191399 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:29])=[C:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[NH:9][C:10]=1[CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=O)C.C[Al](C)C>C1(C)C=CC=CC=1>[C:25]([O:24][C:22]([C:8]1[NH:9][C:10]2[CH2:11][CH2:12][CH2:13][N:14]([CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:4](=[O:3])[C:6]=2[C:7]=1[CH3:29])=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 16682925TrimethylaluminumHCID 498403945-[3-(2-diethylamino-ethylamino)-propyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester

Product 1

HCID 498403955-(2-Diethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carboxylic acid tert-butyl esterYield 75.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

5-[3-(2-Diethylamino-ethylamino)-propyl]-3-methyl-1H-pyrrole-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester 1 h (3.547 g, 8.67 mmol) was dissolved in 70 ml of toluene and stirred for 10 minutes at room temperature under an argon atmosphere. The mixture was added with a solution of trimethyl aluminum in toluene (5.6 ml, 2 mol/L, 11.27 mmol), and stirred for another 30 minutes at room temperature until no white smoke was released. The reaction mixture was heated to reflux for 4 hours in an oil bath. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, quenched with ethanol (10 ml, 95%), and added with anhydrous ethanol (60 ml). The resulting mixture was filtered through a pad of Celite, washed with anhydrous ethanol (200 ml×4) and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 5-(2-diethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carboxylic acid tert-butyl ester 1i (0.413 g, yield 75.7%) as a white solid.

Workup

  1. stirringstirred for another 30 minutes at room temperature until no white smoke
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 4 hours in an oil bath
  4. temperaturethe reaction mixture was naturally cooled down to room temperature
  5. customquenched with ethanol (10 ml, 95%)
  6. additionadded with anhydrous ethanol (60 ml)
  7. filtrationThe resulting mixture was filtered through a pad of Celite
  8. washwashed with anhydrous ethanol (200 ml×4)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c1a0d5e12eda453e842254470f47ad08
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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