Pyridine → HCID 86667787, compound

HRID 1631880Notes

Reaction equation

HRID 1631880 reaction equation
[O:1]=[C:2]1[CH:6]([CH2:7][CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH2:5][CH:4]([O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:3]1[C:22]1[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=1[CH3:30].Cl.[NH2:32][OH:33].N1C=CC=C[CH:35]=1>C(O)C.O>[CH3:35][O:33][N:32]=[C:11]1[CH2:12][CH2:13][CH:8]([CH2:7][CH:6]2[CH2:5][CH:4]([O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:3]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[CH3:30])[C:2]2=[O:1])[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 66898038HCID 66898038, compound

Product 1

HCID 86667787HCID 86667787, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2,2-dimethyl-propionic acid 3-oxo-4-(4-oxo-cyclohexylmethyl)-2-(2,4,6-trimethyl-phenyl)-cyclopentyl ester (150 mg, 0.36 mmol) is dissolved in ethanol (8 ml) and hydroxylamine hydrochloride (36 mg, 0.43 mmol) is added. The solution is stirred while adding pyridine (32 mg, 0.40 mmol). The reaction mixture is heated to reflux for 2 hours. The reaction mixture is diluted with water and extracted with dichloromethane (1×40 ml). The organic extract is dried over magnesium sulphate, filtered and evaporated to a brown gum. The product is purified by HPLC to give 2,2-dimethyl-propionic acid 4-(4-methoxyimino-cyclohexylmethyl)-3-oxo-2-(2,4,6-trimethyl-phenyl)-cyclopentyl ester.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with dichloromethane (1×40 ml)
  4. extractionThe organic extract
  5. dry with materialis dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to a brown gum
  8. customThe product is purified by HPLC

Sources & evidence

ORD record
ord-dacc9b51adac4c458011501b77f8b2f6
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

Loading…