Methylhydrazine → HCID 86686320, compound

HRID 1043880Notes

Reaction equation

HRID 1043880 reaction equation
CNN.O=C1C2C(=CC=CC=2)C(=O)[N:6]1[N:15]([C@H:23]1[CH2:27][CH2:26][O:25][CH2:24]1)[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19]>C1COCC1>[O:25]1[CH2:26][CH2:27][C@H:23]([N:15]([C:16]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:22])[NH2:6])[CH2:24]1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 86686319HCID 86686319, compound

Product 1

HCID 86686320HCID 86686320, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylhydrazine (3.94 mL) was added dropwise to a solution of (S)-t-butyl (1,3-dioxoisoindolin-2-yl)(tetrahydrofuran-3-yl)carbamate (12.3 g) in THF (125 mL) under ice-cooling over two minutes. The reaction mixture was stirred at 0° C. for 30 minutes, at room temperature for three days and then at 50° C. for four hours. The reaction mixture was ice-cooled, and the insoluble matter was then removed from the reaction mixture by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 14%) to give the title compound (7.04 g).

Workup

  1. temperaturecooling over two minutes
  2. waitat 50° C. for four hours
  3. temperaturecooled
  4. customthe insoluble matter was then removed from the reaction mixture by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 14%)

Sources & evidence

ORD record
ord-b8a1782560d543a5a9a540e6ed63668f
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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