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

HRID 749147

반응식

HRID 749147 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-89737a3b41aa4b4ca0bdba7e3185248c
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402592B2

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