Methanol → 4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one

HRID 552896ノート

反応式

HRID 552896 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:16][CH2:17][CH2:18]I)[C:10]2[CH2:14][O:13][C:12](=[O:15])[CH:11]=2)=[CH:4][CH:3]=1.C([N-]C(C)C)(C)C.[Li+].CO>O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:16][CH2:17][CH2:18][CH:14]3[O:13][C:12](=[O:15])[CH:11]=[C:10]23)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 887MethanolHCID 2724682Lithium diisopropylamideHCID 577798354-[[(6-chloropyridin-3-yl)methyl](3-iodopropyl)amino]furan-2(5H)-one

生成物 1

HCID 167527744-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridin-2(4H)-one収率 85%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

31.55 g (80.36 mmol) of 4-[[(6-chloropyridin-3-yl]methyl](3-iodopropyl)amino]furan-2(5H)-one (II-3) are dissolved in 900 ml of tetrahydrofuran and cooled to −78° C., and 42.19 ml (84.38 mmol) of a 2.0M solution of lithium diisopropylamide in tetrahydrofuran are added. After 10 minutes of stirring at −78° C., the mixture is warmed to room temperature and stirred at room temperature for a further 30 minutes. After addition of 20 ml of methanol, the mixture is concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase ethyl acetate gives 18.05 g (85% of theory) of 4-[(6-chloropyridin-3-yl)methyl]-5,6,7,7a-tetrahydrofuro[3,2-b]pyridine-2(4H)-one.

後処理

  1. temperaturethe mixture is warmed to room temperature
  2. stirringstirred at room temperature for a further 30 minutes
  3. concentrationthe mixture is concentrated under reduced pressure
  4. customPurification of the residue by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

出典と根拠

ORDレコード
ord-ca2d3c81769b4d19bf0ec8129f38f786
出典データセット
uspto-grants-2011_05
特許番号
US07951951B2

反応ノート

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