2-Piperidone → HCID 68575842, compound

HRID 2237730Notes

Reaction equation

HRID 2237730 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][C:16]1[CH:39]=[CH:38][C:19]([CH2:20][C@H:21]([CH:35]([CH3:37])[CH3:36])[CH2:22][C@H:23]([NH:27][C:28](=[O:34])[O:29]C(C)(C)C)[C@@H:24]2[CH2:26]O2)=[CH:18][C:17]=1[O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45]>CS(C)=O>[CH3:14][O:15][C:16]1[CH:39]=[CH:38][C:19]([CH2:20][C@H:21]([CH:35]([CH3:37])[CH3:36])[CH2:22][C@H:23]2[C@H:24]([CH2:26][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][C:2]3=[O:7])[O:29][C:28](=[O:34])[NH:27]2)=[CH:18][C:17]=1[O:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45]

Participants

5

Reactant 3

HCID 126652-PiperidoneHCID 23665647Potassium tert-butoxideHCID 59849018HCID 59849018, compound

Product 1

HCID 68575842HCID 68575842, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 0.115 g of piperidin-2-one and 0.136 g of potassium tert-butoxide in 3 ml of dimethyl sulphoxide is stirred at room temperature over 30 minutes, admixed with 0.25 g of tert-butyl {3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methyl-1(S)-(R)-oxiranylpentyl}carbamate (font size changed from Arial 10 to 11) (Example 1b) 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 obtained from the residue by means of flash chromatography (SiO2 60F) as a yellow oil. Rf=0.33 (95:5 dichloromethane-methanol); Rt=3.94 (gradient I).

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-acf546fbd9e345cf92a1ec1f28658b28
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

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