Aluminium lithium hydride → HCID 58190463, compound

HRID 1959644Notes

Reaction equation

HRID 1959644 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12]([NH:14][O:15][CH:16]([CH3:22])[C:17](OCC)=[O:18])=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[OH:18][CH2:17][CH:16]([O:15][NH:14][C:12](=[O:13])[O:11][C:7]([CH3:10])([CH3:9])[CH3:8])[CH3:22]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58190590Ethyl 2-(tert-butoxycarbonylaminooxy)propanoate

Product 1

HCID 58190463HCID 58190463, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of LiAlH4 (213 mg, 5.62 mmol) in anhydrous THF (8 mL) was added slowly to a solution of ethyl 2-(t-butoxycarbonylaminooxy)propanoate (820 mg, 3.52 mmol) in THF (15 mL) at 0° C. The mixture was stirred at 0° C. for 5 h and then at rt overnight. The solution was quenched with a mixture of Na2SO4 and water, and stirred for an additional 1.5 h. The mixture was filtered and concentrated. The crude was dissolved in EtOAc, washed with water and brine, and then dried over Na2SO4. Solvent was evaporated to afford the title compound as a clear oil (500 mg, 74.4%). 1H-NMR (400 MHz, CDCl3) δ ppm 7.09 (s, 1H), 3.95 (m, 1H), 3.69 (dd, 1H), 3.47 (m, 1H), 1.51 (s, 9H), 1.21 (d, 3H).

Workup

  1. customat rt
  2. customovernight
  3. customThe solution was quenched with a mixture of Na2SO4 and water
  4. stirringstirred for an additional 1.5 h
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated
  7. dissolutionThe crude was dissolved in EtOAc
  8. washwashed with water and brine
  9. dry with materialdried over Na2SO4
  10. customSolvent was evaporated

Sources & evidence

ORD record
ord-c6020df0a96846a4bfb1adc8f862920f
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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