Tetrahydrofuran → 2-(N-Boc-aminooxy)-2-methylpropan-1-ol

HRID 79001Notes

Reaction equation

HRID 79001 reaction equation
C([O:3][C:4](=O)[C:5]([O:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:7])[CH3:6])C.[AlH4-].[Li+].O1CCCC1>C(OCC)C>[C:10]([NH:9][O:8][C:5]([CH3:7])([CH3:6])[CH2:4][OH:3])([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 28112Lithium aluminum hydrideHCID 108243852-(N-Boc-aminooxy)isobutyric acid ethyl ester

Product 1

HCID 108458992-(N-Boc-aminooxy)-2-methylpropan-1-olYield 99.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(N-Boc-aminooxy)isobutyric acid ethyl ester (2.35 g, 9.5 mmol) in anhydrous ethyl ether (100 mL) at 0° C. under nitrogen was added 1.0 M lithiumtetrahydroaluminate in tetrahydrofuran (17.1 mL, 17 mmol), and the reaction mixture stirred at 0° C. for 5 hours. The reaction mixture was quenched with water (25 mL) and allowed to warm to room temperature. The suspension was filtered and the residue washed with diethyl ether and layers separated. The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a white solid (1.94 g, 99%). 1H NMR (CDCl3, 400 MHz) 3.40 (s, 2H), 1.50 (s, 9H), 1.20 (s, 6H).

Workup

  1. customThe reaction mixture was quenched with water (25 mL)
  2. temperatureto warm to room temperature
  3. filtrationThe suspension was filtered
  4. washthe residue washed with diethyl ether and layers
  5. customseparated
  6. extractionThe organic extract
  7. dry with materialwas dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-35e1f6823c8d4c0cacedf4d796d1529d
Source dataset
uspto-grants-2014_09
Patent number
US08841462B2

Reaction notes

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