Ethanol → HCID 20748464, compound

HRID 1760045Notes

Reaction equation

HRID 1760045 reaction equation
C(O)C.[Cl-].[NH4+].O1CCCC1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[CH2:19][N:18]([C:25](=[O:41])[C@@H:26]([NH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[N+:38]([O-])=O)[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:17][CH2:16]2>[Fe].O>[NH2:38][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=1[NH:31][C@@H:26]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:25]([N:18]1[CH2:17][CH2:16][C:15]2[C:20](=[CH:21][C:22]([O:23][CH3:24])=[C:13]([O:12][CH3:11])[CH:14]=2)[CH2:19]1)=[O:41]

Participants

7

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 69745485HCID 69745485, compound

Product 1

HCID 20748464HCID 20748464, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Ethanol (5 ml) and a saturated aqueous ammonium chloride solution (5 ml) were added to a tetrahydrofuran (5 ml) solution of (2S)-1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3,3-dimethyl-2-((2-nitrophenyl)amino)butan-1-one (395 mg, 0.92 mmol) obtained in Example 24, and the mixture was stirred at room temperature. Water was added to the reaction solution until the insoluble matter was dissolved, powdery iron (6 g) was added, and the mixture was refluxed with heating for 2 hours. The reaction solution was cooled to room temperature, and the excessive iron and tinorganic salt were filtered off using Celite. The filtrate was diluted with ethyl acetate (150 ml), washed with a 1 N aqueous sodium hydroxide solution (50 ml×2), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography using ethyl acetate and hexane (1:1) and then chloroform and methanol (20:1) as eluents to obtain the captioned compound (321 mg, 87%) as a colorless foamy substance.

Workup

  1. dissolutionwas dissolved
  2. temperaturethe mixture was refluxed
  3. temperaturewith heating for 2 hours
  4. temperatureThe reaction solution was cooled to room temperature
  5. filtrationthe excessive iron and tinorganic salt were filtered off
  6. additionThe filtrate was diluted with ethyl acetate (150 ml)
  7. washwashed with a 1 N aqueous sodium hydroxide solution (50 ml×2)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-12f112601295423eae8535460bcce31a
Source dataset
uspto-grants-2005_01
Patent number
US06838465B2

Reaction notes

Loading…