Triethylamine → HCID 58909938, compound

HRID 1295976Notes

Reaction equation

HRID 1295976 reaction equation
C(N(CC)CC)C.[C:8]([C:12]1[CH:13]=[C:14]([C:31](=[O:33])[CH3:32])[CH:15]=[C:16]([N:20]2[CH2:24][C@@H:23]([O:25][CH2:26][O:27][CH3:28])[C@H:22]([O:29][CH3:30])[CH2:21]2)[C:17]=1[O:18][CH3:19])([CH3:11])([CH3:10])[CH3:9].[Br:34]N1C(=O)CCC1=O>O1CCCC1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[Br:34][CH2:32][C:31]([C:14]1[CH:15]=[C:16]([N:20]2[CH2:24][C@@H:23]([O:25][CH2:26][O:27][CH3:28])[C@H:22]([O:29][CH3:30])[CH2:21]2)[C:17]([O:18][CH3:19])=[C:12]([C:8]([CH3:11])([CH3:9])[CH3:10])[CH:13]=1)=[O:33]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 58909951HCID 58909951, compound

Product 1

HCID 58909938HCID 58909938, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Triethylamine (0.46 ml, 3.3 mmol) and tert-butyl dimethylsilyltrifluoromethanesulfonate (0.37 ml, 1.6 mmol) were added dropwise in that order to a solution of 1-{3-(tert-butyl)-4-methoxy-5-[(3R,4R)-3-methoxy-4-(methoxymethoxy)tetrahydro-1H-1-pyrrolyl]phenyl}-1-ethanone (397 mg, 1.09 mmol) in tetrahydrofuran (4 ml) while cooling on ice, and the mixture was stirred at the same temperature for 20 minutes. N-Bromosuccinimide (290 mg, 1.63 mmol) was then added and stirring was continued at the same temperature for 15 minutes. After completion of the reaction, the mixture was diluted with saturated aqueous sodium hydrogencarbonate and ethyl acetate and the organic layer was separated. The organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (434 mg, 90%) as a light yellow oil.

Workup

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued at the same temperature for 15 minutes
  4. customAfter completion of the reaction
  5. customthe organic layer was separated
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-676570664efa4783bfe4119a3968cd64
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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