3-Bromo-5-phenylpyridine → Ethyl 6-hydroxy-6-(5-phenyl-3-pyridinyl)-3-azabicyclo[3.2.1]octane-3-carboxylate

HRID 749147

Reaction equation

HRID 749147 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.C([Mg]Cl)(C)C.[O:19]=[C:20]1[CH2:26][CH:25]2[CH2:27][CH:21]1[CH2:22][N:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24]2>C1COCC1>[OH:19][C:20]1([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:7]=2)[CH2:26][CH:25]2[CH2:27][CH:21]1[CH2:22][N:23]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24]2

Participants

5

Reactant 3

HCID 27629043-Bromo-5-phenylpyridineHCID 53302214Ethyl 6-oxo-3-azabicyclo(3.2.1)octane-3-carboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 57486356Ethyl 6-hydroxy-6-(5-phenyl-3-pyridinyl)-3-azabicyclo[3.2.1]octane-3-carboxylateYield 14.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 3-bromo-5-phenylpyridine (0.23 g, 1.0 mmol) in THF (5 mL) at ambient temperature was added 2.0 M isopropylmagnesium chloride in THF (0.5 mL). The reaction was stirred for an hour under nitrogen. Then a solution of ethyl 6-oxo-3-azabicyclo[3.2.1]octane-3-carboxylate (0.21 g, 1.0 mmol) in THF (2 mL) was added. The mixture was stirred at ambient temperature overnight, concentrated and quenched with water (1 mL). The mixture was extracted with chloroform (2×10 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated by rotary evaporation. The compound was purified by silica gel column chromatography (1:1 ethyl acetate/hexane) to yield 50 mg of product (13%).

Workup

  1. stirringThe mixture was stirred at ambient temperature overnight
  2. concentrationconcentrated
  3. customquenched with water (1 mL)
  4. extractionThe mixture was extracted with chloroform (2×10 mL)
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe compound was purified by silica gel column chromatography (1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-89737a3b41aa4b4ca0bdba7e3185248c
Source dataset
uspto-grants-2008_07
Patent number
US07402592B2

Linked notes

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