Triethylamine → HCID 69075122, compound

HRID 553965Notes

Reaction equation

HRID 553965 reaction equation
CS(Cl)(=O)=O.C(N(CC)CC)C.O[C@H:14]1[CH2:23][C@@H:22]2[N:17]([C:18](=[O:24])[CH2:19][CH2:20][CH2:21]2)[C@H:16]([C:25]2[CH:30]=[C:29]([F:31])[C:28]([F:32])=[C:27]([F:33])[CH:26]=2)[CH2:15]1>C(Cl)Cl>[F:31][C:29]1[CH:30]=[C:25]([C@@H:16]2[CH:15]=[CH:14][CH2:23][C@@H:22]3[N:17]2[C:18](=[O:24])[CH2:19][CH2:20][CH2:21]3)[CH:26]=[C:27]([F:33])[C:28]=1[F:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69074559HCID 69074559, compound

Product 1

HCID 69075122HCID 69075122, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (776 μL) and triethylamine (2.79 mL) were added to a solution of (6S*,8S*,9aR*)-8-hydroxy-6-(3,4,5-trifluorophenyl)octahydroquinolizin-4-one (1.0 g) in methylene chloride (20 mL) under ice-cooling, and the reaction solution was stirred at room temperature for two hours. The solvent was removed by an evaporator. Then, sodium methoxide (28% solution in methanol, 3.22 g) was added to a mixed solution of the resulting residue in THF-ethanol (17 mL), and the reaction solution was stirred at room temperature for four hours. To make the starting material disappear, sodium methoxide (28% solution in methanol, 5.0 mL) was added to the reaction solution, which was then stirred at room temperature overnight. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system) to obtain 681 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. customThe solvent was removed by an evaporator
  3. additionThen, sodium methoxide (28% solution in methanol, 3.22 g) was added to a mixed solution of the resulting residue in THF-ethanol (17 mL)
  4. stirringthe reaction solution was stirred at room temperature for four hours
  5. additionsodium methoxide (28% solution in methanol, 5.0 mL) was added to the reaction solution, which
  6. stirringwas then stirred at room temperature overnight
  7. additionWater and ethyl acetate were added to the reaction solution
  8. customthe organic layer was separated
  9. washThe resulting organic layer was washed with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-3b160da3d9d147829089606eef513b5e
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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