Hydrazine hydrate (1:1) → 2-[1-(Cyclopropylcarbonyl)-3-azetidinyl]acetohydrazide

HRID 2405368Notes

Reaction equation

HRID 2405368 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]1[CH2:9][N:8]([C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])[CH2:7]1)C.O.[NH2:17][NH2:18]>C(O)C>[CH:12]1([C:10]([N:8]2[CH2:9][CH:6]([CH2:5][C:4]([NH:17][NH2:18])=[O:3])[CH2:7]2)=[O:11])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86715179HCID 86715179, compound

Product 1

HCID 673539452-[1-(Cyclopropylcarbonyl)-3-azetidinyl]acetohydrazideYield 76.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a round bottom flask equipped with reflux condenser under nitrogen, a solution of ethyl[1-(cyclopropylcarbonyl)-3-azetidinyl]acetate (0.433 g, 2.097 mmol) and hydrazine monohydrate (1.3 mL, 41.9 mmol) in ethanol (10 mL) was stirred at 80° C. for 16.5 h. The reaction was cooled to room temperature and concentrated in vacuo. The residue was then concentrated down from methanol and then toluene. The residue was dissolved in dichloromethane, filtered through sodium sulfate, and concentrated in vacuo to a colorless oil. The oil still looked wet and was too heavy, so it was dissolved again in dichloromethane and filtered through sodium sulfate, rinsing with additional dichloromethane. The combined organics were concentrated in vacuo and then concentrated under high vacuum pressure to yield the crude title product as a yellow oil (0.316 g, 86% pure, 66% yield). MS(ES)+ m/e 198.1 [M+H]+, 395.1 [2M+H]+.

Workup

  1. customIn a round bottom flask equipped
  2. temperaturewith reflux condenser under nitrogen
  3. concentrationconcentrated in vacuo
  4. concentrationThe residue was then concentrated down from methanol
  5. dissolutionThe residue was dissolved in dichloromethane
  6. filtrationfiltered through sodium sulfate
  7. concentrationconcentrated in vacuo to a colorless oil
  8. dissolutionwas dissolved again in dichloromethane
  9. filtrationfiltered through sodium sulfate
  10. washrinsing with additional dichloromethane
  11. concentrationThe combined organics were concentrated in vacuo
  12. concentrationconcentrated under high vacuum pressure

Sources & evidence

ORD record
ord-731728868f6c43bd98f9259fa1e84546
Source dataset
uspto-grants-2014_08
Patent number
US08802864B2

Reaction notes

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