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

HRID 552896노트

반응식

HRID 552896 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ca2d3c81769b4d19bf0ec8129f38f786
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951951B2

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