Sodium borohydride → 3-Benzyl-1,2,3,4,5,6-hexahydro-7h-pyrido[3,4-d][2]benzazepin-7-one

HRID 80523ノート

反応式

HRID 80523 の反応式
[Br-].[CH2:2]([N+:9]1[CH:19]=[CH:18][C:17]2[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[C:14](=[O:24])[NH:13][CH2:12][C:11]=2[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C.O>[CH2:2]([N:9]1[CH2:19][CH2:18][C:17]2[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[C:14](=[O:24])[NH:13][CH2:12][C:11]=2[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 672477733-Benzyl-7-oxo-6,7-dihydro-5h-pyrido[3,4-d][2]benzazepin-3-ium bromide

生成物 1

HCID 595485223-Benzyl-1,2,3,4,5,6-hexahydro-7h-pyrido[3,4-d][2]benzazepin-7-one

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

To a suspension of Example 180E (17.7 g, 46.4 mmol) in 200 mL of ethanol/water (4:1) at 0° C. was added NaBH4 (8.9 g, 0.232 mol) portion-wise. After stirring for 0.5 hour, the mixture was quenched with 1N HCl to pH 4-5 and concentrated under reduced pressure. The residue was dissolved in 100 mL of saturated aqueous K2CO3 and extracted with dichloromethane. The organic phase was washed with brine, dried and purified by column chromatography on silica gel eluting with dichloromethane/methanol (30:1) to obtain the title compound.

後処理

  1. customthe mixture was quenched with 1N HCl to pH 4-5
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 100 mL of saturated aqueous K2CO3
  4. extractionextracted with dichloromethane
  5. washThe organic phase was washed with brine
  6. customdried
  7. custompurified by column chromatography on silica gel eluting with dichloromethane/methanol (30:1)

出典と根拠

ORDレコード
ord-651380d075ed45e2a548946c6fd118a6
出典データセット
uspto-grants-2014_09
特許番号
US08846663B2

反応ノート

読み込み中…