Dichloromethane → 3-(2-Hydroxy-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone

HRID 1087777

反応式

HRID 1087777 の反応式
[BH4-].[K+].[CH3:3][O:4][C:5]1[N:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([N:15]3[CH:23]([CH2:24][C:25](=[O:31])[CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16]3=[O:32])=[N:12]2)=[CH:7][CH:6]=1.ClCCl>O.C(O)C>[OH:31][CH:25]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:24][CH:23]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16](=[O:32])[N:15]1[C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[N:14][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[N:12]=1

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 4192641Potassium borohydrideHCID 141821822-(7-Methoxy-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-1-isoindolinone

生成物 1

HCID 141821843-(2-Hydroxy-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone収率 66.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
20 °C

実験手順

Potassium borohydride (0.41 g) dissolved in distilled water (12 cc) is added at a temperature in the region of 20° C. to a suspension of 2-(7-methoxy-1,8-naphthyridin-2-yl)-3-(5-methyl-2-oxohexyl)-1-isoindolinone (3.0 g) in ethanol (50 cc), and the suspension is stirred for 16 hours at a temperature in the region of 20° C. The reaction mixture is then poured into a mixture of distilled water (300 cc) and dichloromethane (150 cc) which has been cooled to a temperature in the region of 0° C. The aqueous phase is separated after settling has occurred, and re-extracted with dichloromethane (2×150 cc). The organic phases are combined, washed with distilled water (3×25 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The product obtained is recrystallized twice in diisopropyl ether. 3-(2-Hydroxy-5-methylhexyl)-2-(7-methoxy-1,8-naphthyridin-2-yl)-1-isoindolinone (2.0 g), m.p. 110° C., is thereby obtained.

後処理

  1. temperaturehas been cooled to a temperature in the region of 0° C
  2. customThe aqueous phase is separated after settling
  3. extractionre-extracted with dichloromethane (2×150 cc)
  4. washwashed with distilled water (3×25 cc)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  8. customThe product obtained
  9. customis recrystallized twice in diisopropyl ether

出典と根拠

ORDレコード
ord-c263b349e8e94a5d901bb0826105edb9
出典データセット
uspto-grants-1990_10
特許番号
US04960779

関連ノート

読み込み中…