Ethanol → HCID 86747056, compound

HRID 2253703Notes

Reaction equation

HRID 2253703 reaction equation
O=[C:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[C@@H:7]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)C.Cl.[NH2:38][OH:39].C([O-])(=O)C.[Na+]>O>[N:38](=[C:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][C@H:8]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])[C@@H:7]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[OH:39]

Participants

6

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 57099534HCID 57099534, compound

Product 1

HCID 86747056HCID 86747056, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere in a round bottom flask were placed 445 mg (1 mmol) of (2S,3S)-1-(4-oxo-4-phenylbut-1-yl)-3-(2methoxybenzylamino)-2-phenylpiperidine and 6 ml of ethanol. To the system were added 209 mg (3.2 mmol) of hydroxylamine hydrochloride and 417 mg (5 mmol) of sodium acetate in 6 ml of H2O, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated and partitioned between chloroform and water. The layers were separated, and the aqueous phase was extracted two times with chloroform. The combined organic extracts were dried (sodium sulfate) and concentrated to 368 mg of gold oil. The crude product was purified by flash column chromatography using 7% in chloroform as the eluant to obtain 174 mg of the title compound as an oil.

Workup

  1. customUnder a nitrogen atmosphere in a round bottom flask were placed
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between chloroform and water
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted two times with chloroform
  6. dry with materialThe combined organic extracts were dried (sodium sulfate)
  7. concentrationconcentrated to 368 mg of gold oil
  8. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-168761e013f144af9f4bda588b8ee114
Source dataset
uspto-grants-1993_08
Patent number
US05232929

Reaction notes

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