Imidazole → HCID 69072025, compound

HRID 553968Notes

Reaction equation

HRID 553968 reaction equation
[OH:1][C@H:2]1[CH2:11][CH2:10][C@@H:9]2[N:4]([C:5](=[O:12])[CH2:6][CH2:7][CH2:8]2)[C@@H:3]1[C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[C:15]([F:21])[CH:14]=1.[CH3:22][C:23]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])[CH3:24].N1C=CN=C1.O>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[Si:26]([O:1][C@H:2]1[CH2:11][CH2:10][C@@H:9]2[N:4]([C:5](=[O:12])[CH2:6][CH2:7][CH2:8]2)[C@@H:3]1[C:13]1[CH:14]=[C:15]([F:21])[C:16]([F:20])=[C:17]([F:19])[CH:18]=1)([C:23]([CH3:25])([CH3:24])[CH3:22])([CH3:28])[CH3:27]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chloride2×HCID 69067548HCID 69067548, compound

Product 1

HCID 69072025HCID 69072025, compoundYield 100.2%

Reagents, catalysts & solvents 3

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

Procedure

A solution of (6R*,7S*,9aR*)-7-hydroxy-6-(3,4,5-trifluorophenyl)octahydroquinolizin-4-one (164 mg), TBSCl (165 mg), imidazole (149 mg), and DMAP (6.7 mg) in DMF (5.0 mL) was stirred at room temperature overnight. To make the starting material disappear, TBSCl (165 mg) 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 227 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->ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-e76697924cc7402ca58eeccfbd237c7a
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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