Imidazole → HCID 69072836, compound

HRID 553857Notes

Reaction equation

HRID 553857 reaction equation
[OH:1][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]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:3]1.N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26].O.C(=O)(O)[O-].[Na+]>CN(C=O)C.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[Si:28]([O:1][C@H: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:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:3]1)([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 69073535HCID 69073535, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 69072836HCID 69072836, compoundYield 54.5%

Reagents, catalysts & solvents 3

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

Procedure

A solution of (6S*,9aR*)-8-hydroxy-6-phenyloctahydroquinolizin-4-one (96.4 mg) in DMF (5.0 mL) was cooled to 0° C. Imidazole (80.3 mg), TBSCl (88.9 mg), and DMAP (4.8 mg) were sequentially added to the reaction solution, which was then stirred at room temperature overnight. 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 77 mg of the title compound. The property values of the compound are as follows.

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-dcf1def04e774c458192e8a2055a00dd
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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