Triethylamine → HCID 66982290, compound

HRID 516227Notes

Reaction equation

HRID 516227 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:23](Cl)(=O)[CH:24]([CH3:26])[CH3:25].C(N(CC)CC)C>ClC(Cl)C.CCOC(C)=O>[CH2:23]([N:1]1[C:10]2[C:5](=[CH:6][C:7]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11][C:8]=3[CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH:24]([CH3:26])[CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 66982459HCID 66982459, compound

Product 1

HCID 66982290HCID 66982290, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 250 mg of t-butyl 1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 2.5 ml of dichloroethane were added 0.175 ml of isobutyryl chloride and 0.4 ml of triethylamine, followed by elevating the temperature to 60° C. and stirring for 30 minutes. The reaction mixture was diluted with EtOAc and washed with 1 M hydrochloric acid, water, a 1 M aqueous sodium hydroxide solution, and saturated brine, and the solvent was concentrated. To the resulting residue was added 2 ml of THF and 3.5 ml of a 1 M solution of a borane-THF complex in THF was added thereto in an ice-bath, followed by stirring at room temperature overnight. The reaction mixture was ice-cooled, and EtOH was added thereto, followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated and the resulting residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 213 mg of t-butyl 1-isobutyl-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate.

Workup

  1. customto 60° C.
  2. washwashed with 1 M hydrochloric acid, water
  3. concentrationa 1 M aqueous sodium hydroxide solution, and saturated brine, and the solvent was concentrated
  4. additionTo the resulting residue was added 2 ml of THF and 3.5 ml of a 1 M solution of a borane-THF complex in THF
  5. additionwas added
  6. customin an ice-bath, followed
  7. stirringby stirring at room temperature overnight
  8. temperaturecooled
  9. additionEtOH was added
  10. stirringby stirring at room temperature for 30 minutes
  11. concentrationThe reaction mixture was concentrated
  12. customthe resulting residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-f7b33ae9166b44ceb5cddd10e21ceca2
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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