Triethylamine → Methyl 4-butyl-1-(methylsulfonyl)-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

HRID 14201Notes

Reaction equation

HRID 14201 reaction equation
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[NH:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[N:8]([S:27]([CH3:26])(=[O:29])=[O:28])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21086196Methyl 4-butyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

Product 1

HCID 21086197Methyl 4-butyl-1-(methylsulfonyl)-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold, stirred solution of methyl 4-butyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate (180 mg) and triethylamine (62 μL) in methylene chloride (2 mL) was added methanesulfonyl chloride (101 μL) and the mixture was stirred for 1 h. The mixture was warmed to room temperature, diluted with methylene chloride, washed with washed with 1 N hydrochloric acid, and brine. The organic layer was then dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes) provided 150 mg of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.57, 7.41, 7.32, 3.90, 3.84, 3.45, 3.38, 1.61, 1.41, 0.98.

Workup

  1. washwashed
  2. washwith washed with 1 N hydrochloric acid, and brine
  3. dry with materialThe organic layer was then dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by flash column chromatography (silica, 1:3 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-417f405e86f84c78a4ab4ee253b1d234
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

Loading…