Benzyl Bromide → Tert-butyl (4-benzyl-2-methoxypyridin-3-yl)carbamate

HRID 2205981노트

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HRID 2205981 반응식
[CH3:1][O:2][C:3]1[C:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][CH:6]=[CH:5][N:4]=1.CN(C)CCN(C)C.CCCCCC.C([Li])CCC.[CH2:36](Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])O.[Na+]>C(OCC)C>[CH2:36]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[C:8]=1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

참가 물질

7

반응물 5

HCID 7498Benzyl BromideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 516892Sodium BicarbonateHCID 11064075tert-Butyl (2-methoxypyridin-3-yl)carbamateHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 10245115Tert-butyl (4-benzyl-2-methoxypyridin-3-yl)carbamate수율 72.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

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온도
0 °C

실험 절차

To a solution of tert-butyl (2-methoxypyridin-3-yl)carbamate (25.1 g) and N,N,N′,N′-tetramethylethane-1,2-diamine (40.6 mL) in diethyl ether (374 mL) was added 1.6M n-butyllithium hexane solution (168 mL) at −78° C., and the mixture was stirred under argon atmosphere at 0° C. for 1 hr. To the reaction mixture was added benzyl bromide (24.9 g) at −78° C., and the mixture was stirred under argon atmosphere at room temperature for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane), and crystallized from ethyl acetate and hexane to give the title compound (25.4 g).

후처리

  1. stirringthe mixture was stirred under argon atmosphere at room temperature for 4 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane)
  7. customcrystallized from ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-b8ce2941a1e843679df7c70fa0c3bb9f
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371320B2

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