Imidazole → HCID 69067824, compound

HRID 553860Notes

Reaction equation

HRID 553860 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:17][CH:16]([OH:18])[CH2:15][C@@H:14]3[N:9]2[C:10](=[O:19])[CH2:11][CH2:12][CH2:13]3)=[CH:4][CH:3]=1.N1C=CN=C1.[CH3:25][C:26]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])[CH3:27].O.C(=O)(O)[O-].[Na+]>CN(C=O)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Si:29]([O:18][C@H:16]1[CH2:15][C@@H:14]2[N:9]([C:10](=[O:19])[CH2:11][CH2:12][CH2:13]2)[C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:17]1)([C:26]([CH3:28])([CH3:27])[CH3:25])([CH3:31])[CH3:30].[Si:29]([O:18][C@@H:16]1[CH2:15][C@@H:14]2[N:9]([C:10](=[O:19])[CH2:11][CH2:12][CH2:13]2)[C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[CH2:17]1)([C:26]([CH3:28])([CH3:27])[CH3:25])([CH3:31])[CH3:30]

Participants

9

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 69068845HCID 69068845, compoundHCID 86585896Sodium bicarbonate water

Product 2

HCID 69067824HCID 69067824, compoundHCID 69073531HCID 69073531, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (6S*,9aR*)-6-(4-fluorophenyl)-8-hydroxyoctahydroquinolizin-4-one (203 mg) in DMF (5.0 mL) was cooled to 0° C. Imidazole (262 mg), TBSCl (291 mg), and DMAP (9.42 mg) were sequentially added to the reaction solution, which was then stirred at room temperature for two hours. Saturated sodium bicarbonate 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 183 mg of (6S*,8S*,9aR*)-8-(tert-butyldimethylsilanyloxy)-6-(4-fluorophenyl)octahydroquinolizin-4-one and 31.8 mg of (6S*,8R*,9aR*)-8-(tert-butyldimethylsilanyloxy)-6-(4-fluorophenyl)octahydroquinolizin-4-one.

Workup

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

Sources & evidence

ORD record
ord-6f29d1a610f64806b73fc35b657f2b67
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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