2-Piperidone → HCID 66888915, compound

HRID 252418Notes

Reaction equation

HRID 252418 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7].CC(C)([O-])C.[K+].[CH3:14][O:15][CH2:16][CH2:17][CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([CH2:28][CH:29]([CH:43]([CH3:45])[CH3:44])[CH2:30][CH:31]([NH:35][C:36](=[O:42])[O:37][C:38](C)([CH3:40])C)C3CO3)[CH:26]=2)[N:21]([CH3:46])[CH:20]=1>CS(C)=O>[CH3:14][O:15][CH2:16][CH2:17][CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([CH2:28][CH:29]([CH:43]([CH3:45])[CH3:44])[CH2:30][CH:31]3[CH:38]([CH2:40][N:1]4[CH2:6][CH2:5][CH2:4][CH2:3][C:2]4=[O:7])[O:37][C:36](=[O:42])[NH:35]3)[CH:26]=2)[N:21]([CH3:46])[CH:20]=1

Participants

5

Reactant 3

HCID 126652-PiperidoneHCID 23665647Potassium tert-butoxideHCID 86618879HCID 86618879, compound

Product 1

HCID 66888915HCID 66888915, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 0.115 g of piperidin-2-one, 0.136 g of potassium tert-butoxide in 3 ml of dimethyl sulphoxide is stirred at room temperature over 30 minutes, admixed with 0.26 g of tert-butyl {3-[3-(3-methoxypropyl)-1-methyl-1H-indol-5-ylmethyl]-4-methyl-1-oxiranylpentyl}carbamate (Example 3Ab) and subsequently stirred further at room temperature overnight. The reaction mixture is poured onto ice-water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed successively with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. stirringsubsequently stirred further at room temperature overnight
  2. additionThe reaction mixture is poured onto ice-water
  3. extractionextracted with tert-butyl methyl ether (2×)
  4. washThe combined organic phases are washed successively with water and brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5536496aa91742ec912eaf6994f33b05
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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