Aluminium lithium hydride → HCID 53728049, compound

HRID 535292Notes

Reaction equation

HRID 535292 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH2:14][C:15](OC(C)(C)C)=[O:16]>C1COCC1.C(OCC)C>[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1)[CH2:14][CH2:15][OH:16]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70983865HCID 70983865, compound

Product 1

HCID 53728049HCID 53728049, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of LAH (lithium aluminum hydride) (1.17 g, 30.8 mmol, 3.0 equiv) in THF (tetrahydrafuran) (45 ml) was added Tert-butyl 2-(di(pyridine-2-yl)amino)acetate (2.9 g, 10.2 mmol) at 0° C. under 1 atm argon (Ar). The reaction was slowly warmed to room temperature over 4 h. The reaction mixture was then diluted with diethyl ether and cooled to 0° C. The reaction was quenched via careful addition of water (4.0 ml) and then dried with magnesium sulfate. The solvent was removed in vacuo, and the crude product was purified by flash chromatography (SiO2, hexane/ethyl acetate=1:1) to afford DPAE as a pale yellow oil. DPAE was obtained (Yield: 1.2 g (55%)), and confirmed by 1H NMR (DMSO-d6, 300 MHz): δ8.27 (m, 2H), 7.62 (m, 2H), 7.16 (d, J=8.4 Hz, 2H), 6.93 (m, 2H), 4.92 (t, J=5.4 Hz, 1H), 4.16 (t, J=6.5 Hz, 2H), 3.58 (q, J=6.5 Hz, 2H). ESI-MS (cation): 216.1 m/z (M+H+) obsd, 215 m/z calcd.

Workup

  1. temperaturecooled to 0° C
  2. customThe reaction was quenched via careful addition of water (4.0 ml)
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified by flash chromatography (SiO2, hexane/ethyl acetate=1:1)
  6. customto afford DPAE as a pale yellow oil
  7. customDPAE was obtained (Yield: 1.2 g (55%))

Sources & evidence

ORD record
ord-6a50ea204bf347eeac8aaf38ef17803b
Source dataset
uspto-grants-2014_10
Patent number
US08859533B2

Reaction notes

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