Borane;tetrahydrofuran → 1-Cyclopropyl-1,2,3,4-tetrahydroquinoxaline

HRID 1877389Notes

Reaction equation

HRID 1877389 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6](=O)[C:5]2=O)[CH2:3][CH2:2]1.B.O1CCCC1>C1COCC1>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 212796951-Cyclopropyl-1,4-dihydroquinoxaline-2,3-dione

Product 1

HCID 673207551-Cyclopropyl-1,2,3,4-tetrahydroquinoxalineYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1-cyclopropyl-1,4-dihydro-quinoxaline-2,3-dione (10.0 g, 49.45 mmol, 1.0 equiv) in THF (500 mL) was added dropwise a 1 M solution of borane-tetrahydrofurane complex (108.8 mL, 108.8 mmol, 2.2 equiv; [CAS RN 14044-65-6]) and the reaction mixture stirred at rt over night. The solvent was removed by evaporation under reduced pressure and the crude reaction mixture extracted from a sat. solution of NaHCO3 (100 mL) with ethyl acetate (3×100 mL). The combined organic phases were dried over Na2SO4 and purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate to give 4.2 g (49%) of the title compound as a light yellow solid. MS (ISP): 175.4 [M+H]+.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe crude reaction mixture
  3. extractionextracted from a sat. solution of NaHCO3 (100 mL) with ethyl acetate (3×100 mL)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. custompurified by silica column chromatography
  6. washeluting with a gradient of heptane/ethyl acetate

Sources & evidence

ORD record
ord-13de2481c9f9467793e4c1da84e92677
Source dataset
uspto-grants-2012_11
Patent number
US08309734B2

Reaction notes

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