Aluminium lithium hydride → HCID 22005325, compound

HRID 324818Notes

Reaction equation

HRID 324818 reaction equation
C[O:2][C:3]([C:5]1[C:6]([CH:28]([CH3:30])[CH3:29])=[N:7][C:8]([CH:25]([CH3:27])[CH3:26])=[C:9]([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:28]([C:6]1[C:5]([CH2:3][OH:2])=[C:10]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[C:9]([CH2:18][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[C:8]([CH:25]([CH3:27])[CH3:26])[N:7]=1)([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22005122HCID 22005122, compound

Product 1

HCID 22005325HCID 22005325, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The intermediate obtained in Step A (375 mg, 0.905 mmol) was dissolved in dry THF (50 mL), treated dropwise with lithium aluminum hydride (1M/THF, 1.81 mL) and the reaction stirred at reflux for 24 hours. The reaction was quenched by the successive dropwise addition of water (0.1 ml), NaOH 20% (0.1 ml), and water again (0.3 ml). Concentration in vacuo afforded a white residue which was partitioned between CH2Cl2 and water. The organic layer was dried with MgSO4, filtered, and concentrated to afford an oil. The product was passed through a pad of silica (40% diethyl ether/hexanes) yielding an oil which slowly solidified to give the title compound as a white solid (295 mg, 0.76 mmol, 84%). 1H NMR (300 MHz, CDCl3): δ 7.14 (m, 4 H), 4.35 (d, 2 H), 3.53 (t, J=4.8 Hz, 4 H), 3.45 (m, 2 H), 3.18 (s, 2 H), 2.18 (t, J=4.5 Hz, 4 H), 1.26 (m, 13 H); FAB-MS calcd for (C23H31N2FO2) 386, found 387 (M+H). Anal. Calcd for C23H31N2O2F: C, 71.47; H, 8.08; N, 7.25; F, 4.92 Found: C, 71.55; H, 8.16; N, 7.05; F, 4.70. mp 93.5-95.5° C. Rf=0.4 (40% diethyl ether/hexane).

Workup

  1. temperatureat reflux for 24 hours
  2. customThe reaction was quenched by the successive dropwise addition of water (0.1 ml), NaOH 20% (0.1 ml), and water again (0.3 ml)
  3. concentrationConcentration in vacuo
  4. customafforded a white residue which
  5. customwas partitioned between CH2Cl2 and water
  6. dry with materialThe organic layer was dried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford an oil
  10. customyielding an oil which

Sources & evidence

ORD record
ord-ba893f0c713a48e79e164bb7681c91be
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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