Methylhydrazine → (S)-tert-butyl 2-(aminooxy)propanoate

HRID 708400Notes

Reaction equation

HRID 708400 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][C@@H:13]([CH3:21])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].CNN>C(Cl)Cl>[NH2:3][O:12][C@@H:13]([CH3:21])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 57751243Propanoic acid,2-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)oxy]-,1,1-dimethylethyl ester,(2S)-

Product 1

HCID 118379554(S)-tert-butyl 2-(aminooxy)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-tert-butyl 2-((1,3-dioxoisoindolin-2-yl)oxy)propanoate (73.3 mg, 0.252 mmol) in DCM (Volume: 500 μL) at 0° C. was added methyl hydrazine (13.5 μL, 0.252 mmol). After stirring for 3 h at 0° C., the solids were filtered off and the filtrate was concentrated in vacuo, affording the title compound (assumed quantitative) as a clear oil.

Workup

  1. filtrationthe solids were filtered off
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8c5f0762f0e644829567bad5d32795ad
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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