Methylhydrazine → t-Butyl 1-(1,4-dioxepan-6-yl)hydrazinecarboxylate

HRID 1043882Notes

Reaction equation

HRID 1043882 reaction equation
CNN.[O:4]1[CH2:10][CH:9]([N:11]([N:19]2C(=O)C3C(=CC=CC=3)C2=O)[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8][O:7][CH2:6][CH2:5]1>C1COCC1>[O:4]1[CH2:10][CH:9]([N:11]([C:12]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:18])[NH2:19])[CH2:8][O:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 86686321t-Butyl 1,4-dioxepan-6-yl(1,3-dioxoisoindolin-2-yl)carbamate

Product 1

HCID 86686322t-Butyl 1-(1,4-dioxepan-6-yl)hydrazinecarboxylateYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylhydrazine (0.21 mL) was added dropwise to a solution of t-butyl 1,4-dioxepan-6-yl(1,3-dioxoisoindolin-2-yl)carbamate (710 mg) in THF (7 mL) over 1 minute. The reaction mixture was stirred at room temperature for 3 days and further stirred at 50° C. for 11 hours. After the reaction mixture was returned to room temperature, the insoluble matter was removed from the reaction mixture by filtration. The filtrate was concentrated under reduced pressure. After toluene was added to the residue, precipitated solid was removed by filtration, The filtrate was purified by silica gel column chromatography (ethyl acetate/n-heptane, 15% to 25%) to give the title compound (393 mg).

Workup

  1. stirringfurther stirred at 50° C. for 11 hours
  2. customwas returned to room temperature
  3. customthe insoluble matter was removed from the reaction mixture by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additionAfter toluene was added to the residue
  6. customprecipitated solid
  7. customwas removed by filtration
  8. customThe filtrate was purified by silica gel column chromatography (ethyl acetate/n-heptane, 15% to 25%)

Sources & evidence

ORD record
ord-ff19e21b77c84d3d9dccf31eb26f0c7c
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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