Indole → HCID 69267751, 화합물

HRID 751524노트

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HRID 751524 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 69267751HCID 69267751, 화합물

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c784b4ff04ff4b939a6d0528e9b0acf9
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405305B2

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