Hydrazine hydrate (1:1) → HCID 86699358, compound

HRID 333993Notes

Reaction equation

HRID 333993 reaction equation
[CH2:1]([N:8]([CH2:16][C@H:17]([N:19]1C(=O)C2C(=CC=CC=2)C1=O)[CH3:18])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CO>[NH2:19][C@H:17]([CH3:18])[CH2:16][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86699356HCID 86699356, compound

Product 1

HCID 86699358HCID 86699358, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

278 mg of (R)-tert-butyl benzyl{2-(1,3-dioxoisoindolin-2-yl)propyl}carbamate was dissolved in 5 mL of methanol. To the solution, 1 mL of hydrazine hydrate was added, and the mixture was stirred at 80° C. for 12 hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. A 10% aqueous potassium hydroxide solution was added thereto, followed by extraction with dichloromethane (40 mL×3). The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (dichloromethane:methanol=2:1) to obtain 147 mg of the title compound as a colorless oil (79%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionA 10% aqueous potassium hydroxide solution was added
  4. extractionfollowed by extraction with dichloromethane (40 mL×3)
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe obtained crude product
  10. customwas purified by silica gel column chromatography (dichloromethane:methanol=2:1)

Sources & evidence

ORD record
ord-c865f83811ff4be79cadc754d05f04ec
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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