2-Chloro-5-nitropyridine → 2-methyl-2-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid ethyl ester

HRID 1691853노트

반응식

HRID 1691853 반응식
[CH2:1]([O:3][C:4](=[O:14])[C:5]([CH3:13])([CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)[CH3:6])[CH3:2].Cl[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:1]([O:3][C:4](=[O:14])[C:5]([CH3:13])([CH:7]1[CH2:12][CH2:11][N:10]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][N:17]=2)[CH2:9][CH2:8]1)[CH3:6])[CH3:2]

참가 물질

5

반응물 3

HCID 783082-Chloro-5-nitropyridineHCID 81531DiisopropylethylamineHCID 49759624Ethyl 2-methyl-2-(piperidin-4-YL)propanoate

생성물 1

HCID 667385542-methyl-2-(5'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-4-yl)-propionic acid ethyl ester수율 92%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
140 °C

실험 절차

The above 2-methyl-2-piperidin-4-yl-propionic acid ethyl ester (606 mg, 3.82 mmol) was mixed with 2-chloro-5-nitropyridine (760 mg, 3.82 mmol) in 10 mL of tetrahydrofuran. To this solution was added diisopropylethylamine (1.33 mL). The mixture was heated in a microwave at 140° C. for 30 minutes. Solvents were evaporated and the residue was extracted with methylene chloride and water. The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified using flash chromatography (eluting with ethyl acetate and hexanes) to give 2-methyl-2-(5′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl)-propionic acid ethyl ester as a solid (1.13 g, 92%). The NMR spectrum obtained on the sample is compatible with its structure.

후처리

  1. customSolvents were evaporated
  2. extractionthe residue was extracted with methylene chloride and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. washflash chromatography (eluting with ethyl acetate and hexanes)

출처 및 근거

ORD 기록
ord-4da59f1da9e949b4a45f61da7cd4df81
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153644B2

반응 노트

불러오는 중…