Aluminium lithium hydride → 3-(2-Aminoethyl)-N-benzyloxetan-3-amine

HRID 539992Notes

Reaction equation

HRID 539992 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:14][C:15]1([CH2:19][C:20]#[N:21])[CH2:18][O:17][CH2:16]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(OCC)C>[NH2:21][CH2:20][CH2:19][C:15]1([NH:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:18][O:17][CH2:16]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 712544323-(Benzylamino)oxetan-3-acetonitrile

Product 1

HCID 712545123-(2-Aminoethyl)-N-benzyloxetan-3-amineYield 90.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cooled slurry of lithium aluminium hydride (327 mg, 8.6 mmol) in anhydrous diethyl ether (40 mL), was added a solution of 3-(benzylamino)oxetan-3-acetonitrile (1.0 g, 4.3 mmol) in anhydrous diethyl ether (10 mL) dropwise at 0° C. After being stirred at 0° C. for 2 hours, the reaction was quenched by introducing disodium sulfate decahydrate slowly. After being stirred for 30 minutes, the mixture was filtered, and the filter cake was washed with ethyl acetate. The filtrate was dried over sodium sulfate and concentrated in vacuo. The residue was purified by flash column to afford 800 mg of 3-(aminoethyl)-N-benzyloxetan-3-amine as a light yellow oil (yield was 79%).

Workup

  1. customthe reaction was quenched
  2. additionby introducing disodium sulfate decahydrate slowly
  3. stirringAfter being stirred for 30 minutes
  4. filtrationthe mixture was filtered
  5. washthe filter cake was washed with ethyl acetate
  6. dry with materialThe filtrate was dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-4597f35ae2f94329927cb432571b5e96
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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