Hydrazine hydrate (1:1) → HCID 71087134, compound

HRID 2405398Notes

Reaction equation

HRID 2405398 reaction equation
[CH:1]1([C:4]([N:6]2[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([O:14]CC)=O)[CH2:7]2)=[O:5])[CH2:3][CH2:2]1.O.[NH2:18][NH2:19]>C(O)C.ClCCl>[CH:1]1([C:4]([N:6]2[CH2:10][CH2:9][C@H:8]([CH2:11][C:12]([NH:18][NH2:19])=[O:14])[CH2:7]2)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86674831HCID 86674831, compound

Product 1

HCID 71087134HCID 71087134, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

In a round bottom flask equipped with reflux condenser, a yellow solution of ethyl [(3R)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetate (2.095 mmol) in ethanol (5 mL) was treated with hydrazine monohydrate (41.9 mmol). The resultant yellow solution was stirred at 80° C. (reflux) overnight. The reaction was cooled to room temperature and concentrated in vacuo. Ethanol (10 mL) was added and the reaction was concentrated to give a clear oil. The oil was dissolved in dichloromethane (white solution observed), dried over magnesium sulfate, filtered, and concentrated in vacuo to give the title compound as a clear oil (quantitative). MS(ES)+ m/e 212.1 [M+H]+, 423.2 [2M+H]+.

Workup

  1. customIn a round bottom flask equipped
  2. temperaturewith reflux condenser
  3. temperature(reflux) overnight
  4. temperatureThe reaction was cooled to room temperature
  5. concentrationconcentrated in vacuo
  6. additionEthanol (10 mL) was added
  7. concentrationthe reaction was concentrated
  8. customto give a clear oil
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26dd6458866648b39b9fc37e1f886a4c
Source dataset
uspto-grants-2014_08
Patent number
US08802864B2

Reaction notes

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