Methylhydrazine → 391212-47-8

HRID 1821826Notes

Reaction equation

HRID 1821826 reaction equation
[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:9][CH2:10][O:11][N:12]1C(=O)C2C(=CC=CC=2)C1=O)[CH3:8])([CH3:4])([CH3:3])[CH3:2].CNN>C(Cl)Cl.CO>[C:1]([O:5][C:6](=[O:23])[N:7]([CH2:9][CH2:10][O:11][NH2:12])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 59846673Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)ethyl(methyl)carbamate

Product 1

HCID 23398498391212-47-8Yield 90.1%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To an ice-cold solution of tert-butyl[2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]ethyl]methylcarbamate (4.3 g, 13=mmol) in CH2Cl2/MeOH (8:2, 90 mL) was added methylhydrazine (3.2 mL, 60 mmol) dropwise. The stirred reaction mixture was allowed to warm to ambient temperature. After 1.5 h, the reaction mixture was concentrated under reduced pressure. To the residue was added CH2Cl2 (35 mL) and the resulting white solid was collected by vacuum filtration. The filtrate was concentrated and purified by column chromatography (silica gel, 50:50 hexanes/EtOAc to 35:65 hexanes/EtOAc) to afford tert-butyl[2-(aminooxy)ethyl]methylcarbamate (2.3 g, 90%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 1.46 (9H, s), 1.82-1.98 (1H, m), 2.88 (3H, br s), 3.44-3.46 (2H, m), 3.74 (2H, t, J=5.3 Hz), 5.44-5.77 (2H, m).

Workup

  1. customThe stirred reaction mixture
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue was added CH2Cl2 (35 mL)
  4. filtrationthe resulting white solid was collected by vacuum filtration
  5. concentrationThe filtrate was concentrated
  6. custompurified by column chromatography (silica gel, 50:50 hexanes/EtOAc to 35:65 hexanes/EtOAc)

Sources & evidence

ORD record
ord-6e5ef49cb6b64c86ac4053fd8d42c2d1
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

Loading…