Water → Methyl 3-bromo-10-isobutyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate

HRID 1182360노트

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HRID 1182360 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:21]=O)[C:5]([N:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:6][CH:7]=1.C[O-].[Na+].O>C(=O)(OC)OC.CO>[Br:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:9][CH2:10][CH2:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:21][C:4]=2[CH:3]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 86604826HCID 86604826, 화합물

생성물 1

HCID 69425256Methyl 3-bromo-10-isobutyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate수율 92.7%

시약·촉매·용매 2

HCID 887Methanol용매HCID 12021Dimethyl Carbonate용매

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온도
65 °C

실험 절차

To a solution of methyl 5-[(5-bromo-3-formylpyridin-2-yl)(isobutyl)amino]pentanoate (840 mg) in dimethyl carbonate (20 ml) was added a 28% sodium methoxide solution in methanol (874 mg), and the mixture was heated at 65° C. for 3 hours under a nitrogen atmosphere. The mixture was returned to room temperature, water was added, and then the resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain the residue, and then the obtained residue was washed with hexane-ethyl acetate to give methyl 3-bromo-10-isobutyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate (741 mg) as yellow crystals.

후처리

  1. customwas returned to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)
  7. customto obtain the residue
  8. washthe obtained residue was washed with hexane-ethyl acetate

출처 및 근거

ORD 기록
ord-c4d8b66a5a0f41c9a471bd169a5231ed
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288654B2

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