Triethylamine → HCID 69075125, compound

HRID 553944Notes

Reaction equation

HRID 553944 reaction equation
O[CH:2]1[CH2:11][C@H:10]2[N:5]([C:6](=[O:12])[CH2:7][CH2:8][CH2:9]2)[C@H:4]([C:13]2[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([F:21])[CH:14]=2)[CH2:3]1.C(N(CC)CC)C.CS(Cl)(=O)=O.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C.O>[F:19][C:17]1[CH:18]=[C:13]([C:4]2[N:5]3[C@H:10]([CH2:11][CH2:2][CH:3]=2)[CH2:9][CH2:8][CH2:7][C:6]3=[O:12])[CH:14]=[C:15]([F:21])[C:16]=1[F:20]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 69074407HCID 69074407, compound

Product 1

HCID 69075125HCID 69075125, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (6S*,9aS*)-8-hydroxy-6-(3,4,5-trifluorophenyl)octahydroquinolizin-4-one obtained in Examples 13 and 14 (3.57 g) in THF (30 mL) was cooled to 0° C. Triethylamine (3.2 mL) and methanesulfonyl chloride (1.3 mL) were added to the reaction solution, which was then stirred at room temperature for 30 minutes. Potassium tert-butoxide (3.9 g) and THF (60 mL) were added to the reaction mixture, and the reaction mixture was heated under reflux for 80 minutes and left to cool. Then, 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) to obtain 1.65 g of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 80 minutes
  3. waitleft
  4. temperatureto cool
  5. customthe organic layer was separated
  6. washThe resulting organic layer was washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-b611353ebd62492da61e58fbc0f85d28
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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