Diethyl Ether → HCID 178511716, compound

HRID 1631433Notes

Reaction equation

HRID 1631433 reaction equation
[CH:1]1([CH2:4][O:5][C@H:6]2[CH2:11][CH2:10][C@H:9]([N:12]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.O.NN.CCOCC>CCO>[CH:1]1([CH2:4][O:5][C@H:6]2[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8][CH2:7]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24654Hydrazine hydrate (1:1)HCID 178515018HCID 178515018, compound

Product 1

HCID 178511716HCID 178511716, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A stirred solution of 12C (620 mg, 2.071 mmol) in EtOH (10 mL) was treated with hydrazine monohydrate (0.152 mL, 3.11 mmol) and stirred at 70° C. for 1 h. The reaction was judged complete by LCMS. Upon cooling, Et2O was added, and reaction was stirred at room temperature for 1 h. The resulting white solid was removed by filtration, and the filtrate was concentrated. The residue was triturated with Et2O, the small amount of white solid was filtered, and the filtrate was concentrated to provide 12D (120 mg, 34% yield) as pale brown oil. 1H NMR (400 MHz, CDCl3) δ ppm 3.11 (d, 2H, J=6.8 Hz); 2.99-3.08 (m, 1H); 2.48-2.57 (m, 1H); 1.64-1.89 (m, 6H); 1.06-1.18 (m, 2H); 0.81-1.02 (m, 3H); 0.31-0.39 (m, 2H); −0.02-0.04 (m, 2H).

Workup

  1. temperatureUpon cooling
  2. customreaction
  3. stirringwas stirred at room temperature for 1 h
  4. customThe resulting white solid was removed by filtration
  5. concentrationthe filtrate was concentrated
  6. customThe residue was triturated with Et2O
  7. filtrationthe small amount of white solid was filtered
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-10b8c4cc9c2c4620b72c2cd7e40cd8a4
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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