Triethylamine → HCID 86601498, compound

HRID 1295982Notes

Reaction equation

HRID 1295982 reaction equation
C(N(CC)CC)C.[C:8]([C:12]1[CH:13]=[C:14]([C:32](=[O:34])[CH3:33])[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][CH2:30][CH3:31])[CH2:21]2)[C:17]=1[O:18][CH3:19])([CH3:11])([CH3:10])[CH3:9].[Br:35]N1C(=O)CCC1=O>O1CCCC1.C(=O)([O-])O.[Na+].C(OCC)(=O)C>[Br:35][CH2:33][C:32]([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][CH2:30][CH3:31])[CH2:21]2)[C:17]([O:18][CH3:19])=[C:12]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:13]=1)=[O:34]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 67184N-bromobutanimideHCID 67136588HCID 67136588, compound

Product 1

HCID 86601498HCID 86601498, compoundYield 101.4%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Triethylamine (0.52 ml, 3.7 mmol) and tert-butyl dimethylsilyltrifluoromethanesulfonate (0.51 ml, 2.2 mmol) were added dropwise in that order to a solution of 1-{3-(tert-butyl)-5-[(3S,4S)-3-ethoxy-4-(methoxymethoxy)tetrahydro-1H-1-pyrrolyl]-4-methoxyphenyl}-1-ethanone (650 mg, 1.71 mmol) in tetrahydrofuran (7 ml) while cooling on ice, and the mixture was stirred at the same temperature for 25 minutes. N-bromosuccinimide (427 mg, 2.40 mmol) was then added and stirring was continued at the same temperature for 25 minutes. After completion of the reaction, the reaction 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 residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (795 mg, 100%) as a light yellow oil.

Workup

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued at the same temperature for 25 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. customThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6724badd583843cfa0c00651160f8d0b
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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