Indole → HCID 69267751、化合物

HRID 751524ノート

反応式

HRID 751524 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]([O:14][C:15]([N:17]1[CH:22](C)[CH2:21][C:20](=O)[CH2:19][CH:18]1C)=[O:16])([CH3:13])([CH3:12])[CH3:11].[C:26](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:27].[Na+].[OH-].[Na+]>C(O)(=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:21]([CH2:26][CH3:27])[CH2:22]1)=[O:16])([CH3:11])([CH3:12])[CH3:13]

参加物

6

反応物 4

HCID 798IndoleHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 59662193tert-Butyl 2,6-dimethyl-4-oxopiperidine-1-carboxylate

生成物 1

HCID 69267751HCID 69267751、化合物

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
70 °C

実験手順

Dissolve 1H-Indole (10 g, 50.2 mmol) and 2,6-Dimethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (8.62 g, 55.2 mmol) in glacial acetic acid (100 mL), add sodium triacetoxyborohydride (15.96 g, 75.3 mmol) and heat the mixture to 70° C. for 20 h. Cool the reaction mixture in an ice bath and made basic with 5N sodium hydroxide solution. Extract the mixture with methylene chloride, wash with water, brine and dry over sodium sulphate to yield the title compound. Flash chromatography using a gradient of ethyl acetate in hexanes yields the pure product. ESMS m/z (relative intensity) ES(M++H): 329.1.

後処理

  1. temperatureCool the reaction mixture in an ice bath
  2. extractionExtract the mixture with methylene chloride
  3. washwash with water, brine
  4. dry with materialdry over sodium sulphate

出典と根拠

ORDレコード
ord-c784b4ff04ff4b939a6d0528e9b0acf9
出典データセット
uspto-grants-2008_07
特許番号
US07405305B2

反応ノート

読み込み中…