Indole → HCID 69267751, compound

HRID 751524Notes

Reaction equation

HRID 751524 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 69267751HCID 69267751, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c784b4ff04ff4b939a6d0528e9b0acf9
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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