Diethyl Ether → tert-butyl N-[2-(aminooxy)ethyl]-N-methylcarbamate

HRID 2218460Notes

Reaction equation

HRID 2218460 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(OCC)C>ClCCl>[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

5

Reactant 3

HCID 3283Diethyl EtherHCID 6061MethylhydrazineHCID 59846673Tert-butyl 2-(1,3-dioxoisoindolin-2-yloxy)ethyl(methyl)carbamate

Product 1

HCID 23398498tert-butyl N-[2-(aminooxy)ethyl]-N-methylcarbamateYield 106.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-ethyl]-methyl-carbamic acid tert-butyl ester (4.50 g, 14.0 mmol) in dichloromethane (40 mL) was treated with methylhydrazine (0.78 mL, 14.7 mmol) and the reaction mixture was stirred 6 h at ambient temperature. Diethyl ether (80 mL) was added and the heterogeneous solution was allowed to stand overnight. The precipitate was removed by filtration and was washed with ether (80 mL). The filtrate was further concentrated and the resultant precipitate was filtered and the second filtrate concentrated to afford (2-Aminooxy-ethyl)-methyl-carbamic acid tert-butyl ester (2.83 g) as a viscous oil: 1H NMR (400 MHz, CDCl3) δ 3.73 (t, J=5.2 Hz, 2 H), 5.45 (br s, NH2), 3.46 and 3.42 (br s, 2 H), 2.86 br s, 3 H), 1.25 (br s, 9 H); MS (APCI+)=191.1.

Workup

  1. waitto stand overnight
  2. customThe precipitate was removed by filtration
  3. washwas washed with ether (80 mL)
  4. concentrationThe filtrate was further concentrated
  5. filtrationthe resultant precipitate was filtered
  6. concentrationthe second filtrate concentrated

Sources & evidence

ORD record
ord-48b7fb5fe077498d9ff6f7ca7add6525
Source dataset
uspto-grants-2008_08
Patent number
US07411001B2

Reaction notes

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