Ethanol → HCID 73155326, compound

HRID 2171277Notes

Reaction equation

HRID 2171277 reaction equation
O.NN.C(O)C.[C:7]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2C(=O)C3C(=CC=CC=3)C2=O)[CH:12]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:11]1)(=[O:9])[CH3:8]>C(OCC)(=O)C>[C:7]([N:10]1[CH2:15][CH2:14][CH:13]([NH2:16])[CH:12]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:11]1)(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 131732940HCID 131732940, compound

Product 1

HCID 73155326HCID 73155326, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Hydrazine monohydrate (1 ml) was added to an ethanol (5 ml) solution containing tert-butyl (1-acetyl-4-(1,3-dioxoisoindolin-2-yl)piperidin-3-yl)carbamate (301 mg) obtained in the 3rd step, followed by heating and stirring at 50° C. for 0.5 hours. Ethyl acetate was added to the reaction solution. The reaction solution was washed with water and saturated saline and dried over anhydrous sodium sulfate. Next, the solvent was distilled away under reduced pressure. Colorless oily matter of tert-butyl (1-acetyl-4-aminopiperidin-3-yl)carbamate (147 mg) was thus obtained.

Workup

  1. customobtained in the 3rd step
  2. temperatureby heating
  3. washThe reaction solution was washed with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationNext, the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-fea02d7aa9b0424c885b26372d27d6d5
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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