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

HRID 1182363노트

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HRID 1182363 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:20]=O)[C:5]([N:8]([CH2:17][CH2:18][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][CH2:18][CH3:19])[CH2:9][CH2:10][CH2:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:20][C:4]=2[CH:3]=1

참가 물질

6

반응물 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 86604827Methyl 5-[(5-bromo-3-formylpyridin-2-yl)(propyl)amino]pentanoate

생성물 1

HCID 69425413Methyl 3-bromo-10-propyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate수율 99.9%

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)(propyl)amino]pentanoate (880 mg) in dimethyl carbonate (20 ml) was added a 28% sodium methoxide solution in methanol (951 mg), and the mixture was heated at 65° C. for 6 hours under a nitrogen atmosphere. The mixture was returned to room temperature, water was added thereto, and then the 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 give methyl 3-bromo-10-propyl-7,8,9,10-tetrahydropyrido[2,3-b]azocine-6-carboxylate (835 mg) as a yellow oily material.

후처리

  1. customwas returned to room temperature
  2. extractionthe 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)

출처 및 근거

ORD 기록
ord-d820e4ccb5034f74b1dafa8e41825f1b
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07288654B2

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