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 1641772ノート

反応式

HRID 1641772 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
140 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-f25989b9d03b423997f0344120424709
出典データセット
uspto-grants-2012_02
特許番号
US08115011B2

反応ノート

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