Diethyl Ether → 391212-47-8

HRID 1062283Notes

Reaction equation

HRID 1062283 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 23398498391212-47-8Yield 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, 2H), 5.45 (br s, NH2), 3.46 and 3.42 (br s, 2H), 2.86 br s, 3H), 1.25 (br s, 9H); 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-8c56a1fac49e4f2bb809233a1e7dda06
Source dataset
uspto-grants-2005_11
Patent number
US06960614B2

Reaction notes

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