Water → HCID 69074875, compound

HRID 553917Notes

Reaction equation

HRID 553917 reaction equation
C(N(CC)CC)C.[Si:8]([O:15]S(C(F)(F)F)(=O)=O)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9].[F:23][C:24]1[CH:29]=[CH:28][C:27]([C@@H:30]2[CH2:39][C@@:38](O)([CH3:40])[CH2:37][C@@H:36]3[N:31]2[C:32](=[O:42])[CH2:33][CH2:34][CH2:35]3)=[CH:26][CH:25]=1.O>C1COCC1.C(OCC)(=O)C>[Si:8]([O:15][C@:38]1([CH3:40])[CH2:37][C@@H:36]2[N:31]([C:32](=[O:42])[CH2:33][CH2:34][CH2:35]2)[C@H:30]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[CH2:39]1)([C:11]([CH3:12])([CH3:13])[CH3:14])([CH3:9])[CH3:10]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 69077389HCID 69077389, compound

Product 1

HCID 69074875HCID 69074875, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (201 μL) and TBSOTf (286 mg) were added to a solution of (6S*,8R*,9aR*)-6-(4-fluorophenyl)-8-hydroxy-8-methyloctahydroquinolizin-4-one (100 mg) in THF (1.0 mL) under ice-cooling, and the reaction solution was stirred for one hour and 50 minutes. 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 116 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThe resulting organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system->ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-2ff3331e2853469d8b2d918b2bf746cf
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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