Ethanol → HCID 58495251, compound

HRID 516222Notes

Reaction equation

HRID 516222 reaction equation
[Cl:1][C:2]1[C:3]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13][C:4]=2[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=O)[CH2:8][CH2:7]2.CCO.[OH-].[Na+]>C1COCC1.O>[Cl:1][C:2]1[C:3]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13][C:4]=2[CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 58495308HCID 58495308, compound

Product 1

HCID 58495251HCID 58495251, compoundYield 118%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.772 g of t-butyl 11-chloro-2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate in 10 ml of THF was added 10.1 ml of a 1 M solution of a borane-THF complex in THF under ice-cooling, followed by elevating to room temperature and stirring for 3 hours. To the reaction mixture was added dropwise 10 ml of EtOH, and subsequently 10 ml of a 1 M aqueous sodium hydroxide solution was added dropwise thereto, followed by stirring. The mixed solution was diluted with water, followed by extraction with EtOAc. The organic layer was dried over anhydrous sodium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 2.007 g of t-butyl 11-chloro-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate as a colorless viscous substance.

Workup

  1. temperaturecooling
  2. customby elevating to room temperature
  3. additionwas added dropwise
  4. stirringby stirring
  5. extractionfollowed by extraction with EtOAc
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-f5df99eafda04497b7fe274b799235bf
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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