Diethyl Ether → 1-(Aminooxy)-3,3-dimethylbutan-2-ol

HRID 494739Notes

Reaction equation

HRID 494739 reaction equation
[OH:1][CH:2]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:3][O:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.CNN.C(OCC)C>ClCCl>[NH2:5][O:4][CH2:3][CH:2]([OH:1])[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6061MethylhydrazineHCID 211115332-(2-Hydroxy-3,3-dimethylbutoxy)-isoindole-1,3-dione

Product 1

HCID 211115321-(Aminooxy)-3,3-dimethylbutan-2-olYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-hydroxy-3,3-dimethylbutoxy)-isoindole-1,3-dione (1.47 g, 5.60 mmol) in dichloromethane (20 mL) cooled to 0° C. was added methylhydrazine (0.31 mL, 5.90 mmol). The white suspension was allowed to stir for 16 hours at room temperature. Diethyl ether (50 mL) was added and the solids were removed by filtration. The filtrate was concentrated, diluted with diethyl ether and the solids were removed by filtration. This procedure was repeated twice more and the final filtrate was concentrated to provide the desired product as a yellow liquid (0.643 g, 86%). 1H NMR (400 MHz, CDCl3) δ 4.87 (br s, 2H), 3.85 (q, 1H), 3.58 (q, 2H), 0.93 (s, 9H).

Workup

  1. customthe solids were removed by filtration
  2. concentrationThe filtrate was concentrated
  3. additiondiluted with diethyl ether
  4. customthe solids were removed by filtration
  5. concentrationthe final filtrate was concentrated

Sources & evidence

ORD record
ord-2ca3e4f120a2409a8e8d1a205e5f52a7
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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