Hydrochloric Acid → HCID 18377306, compound

HRID 2301095Notes

Reaction equation

HRID 2301095 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:25][CH2:24][N:14]2[C:15]3[C:20]([NH:21][C:22](=O)[CH:13]2[CH2:12]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:33][C:34]([F:39])([F:38])[C:35](O)=[O:36].Cl>ClCCl.C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:25][CH2:24][N:14]2[C:15]3[C:20]([N:21]([C:35](=[O:36])[C:34]([F:39])([F:38])[F:33])[CH2:22][CH:13]2[CH2:12]1)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 121096443-benzyloxycarbonyl-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one

Product 1

HCID 18377306HCID 18377306, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 2 ml portion of THF solution containing 100 mg (0.30 mmol) of 3-benzyloxycarbonyl-2,3,4,4a-tetrahydro-1H-pyrazino[1,2-a]quinoxalin-5(6H)-one was cooled to 0° C., mixed with 59 μl (0.59 mmol) of borane-dimethyl sulfide complex and stirred overnight at room temperature. The reaction solution was mixed with ice water, stirred for 30 minutes and extracted with ethyl acetate. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure, and the thus obtained residue was recrystallized from ethyl acetate-hexane to obtain crude crystals. A 97 mg portion of the crude crystals were dissolved in 2 ml of dichloromethane, and the solution was mixed with 125 μl (0.90 mmol) of triethylamine and 64 μl (0.45 mmol) of anhydrous trifluoroacetic acid and stirred overnight at room temperature. The reaction solution was poured into ice water, acidified by adding 1 N hydrochloric acid and then extracted with ethyl acetate. After drying (Na2SO4), the solvent was removed by evaporation under a reduced pressure, and the thus obtained residue was purified by a silica gel chromatography (30 cc; elution by ethyl acetate-hexane=1:5) to obtain 94 mg (74% in yield) of the title compound.

Workup

  1. additionmixed with 59 μl (0.59 mmol) of borane-dimethyl sulfide complex
  2. stirringstirred for 30 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialAfter drying (Na2SO4)
  5. customthe solvent was removed by evaporation under a reduced pressure
  6. customthe thus obtained residue was recrystallized from ethyl acetate-hexane
  7. customto obtain crude crystals
  8. stirringstirred overnight at room temperature
  9. extractionextracted with ethyl acetate
  10. dry with materialAfter drying (Na2SO4)
  11. customthe solvent was removed by evaporation under a reduced pressure
  12. customthe thus obtained residue was purified by a silica gel chromatography (30 cc; elution by ethyl acetate-hexane=1:5)
  13. customto obtain

Sources & evidence

ORD record
ord-a0ad22e8215d4c3c9e625c76edd9b20f
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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