N-bromobutanimide → HCID 58911537, compound

HRID 1296322Notes

Reaction equation

HRID 1296322 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@@H:8]3[CH2:17][NH:16][CH2:15][CH2:14][N:9]3[C:10](=[O:13])[C:11]=2[CH:12]=1.C1C(=O)N([Br:27])C(=O)C1>OS(O)(=O)=O>[Br:27][C:5]1[C:6]2[CH2:7][C@@H:8]3[CH2:17][NH:16][CH2:15][CH2:14][N:9]3[C:10](=[O:13])[C:11]=2[CH:12]=[C:3]([C:2]([F:1])([F:18])[F:19])[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11176570HCID 11176570, compound

Product 1

HCID 58911537HCID 58911537, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of (R)-8 trifluoromethyl-1,2,3,4,11,11a-hexahydro-pyrazino[1,2-b]isoquinolin-6-one (245 mg, 0.9 mmol) in H2SO4 (2 mL) was treated with NBS (210 mg, 1.17 mmol) at room temperature. After 48 h, the reaction mixture was quenched with saturated aqueous NaHCO3 and diluted with EtOAc (15 mL). The solution was extracted with EtOAc (50 mL) and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to afford a yellow oil. Purification of the oil by flash column chromatography (SiO2, 96:4:1 methylene chloride/methanol/triethylamine) provided (R)-10-bromo-8-trifluoromethyl-1,2,3,4,11,11a-hexahydropyrazino[1,2-b]isoquinolin-6-one (80 mg, 25%) as an off-white solid. MS (ESI) 349 (M+H).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous NaHCO3
  2. additiondiluted with EtOAc (15 mL)
  3. extractionThe solution was extracted with EtOAc (50 mL)
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil
  8. customPurification of the oil by flash column chromatography (SiO2, 96:4:1 methylene chloride/methanol/triethylamine)

Sources & evidence

ORD record
ord-f81bf85e85964b87896ad3bed764fc82
Source dataset
uspto-grants-2007_07
Patent number
US07244843B2

Reaction notes

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