Aluminium lithium hydride → HCID 67418229, compound

HRID 1429358Notes

Reaction equation

HRID 1429358 reaction equation
[CH2:1]([CH:8]1[CH2:15][N:14]([CH3:16])[C:13](=O)[C:12]2[CH:18]=[CH:19][CH:20]=[CH:21][C:11]=2[CH2:10][N:9]1[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH3:32])(=[O:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:1]([CH:8]1[N:9]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH3:32])(=[O:24])=[O:23])[CH2:10][C:11]2[CH:21]=[CH:20][CH:19]=[CH:18][C:12]=2[CH2:13][N:14]([CH3:16])[CH2:15]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67419119HCID 67419119, compound

Product 1

HCID 67418229HCID 67418229, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of compound 2h (150 mg, 0.33 mmol) in tetrahydrofuran (10 mL) at 5° C., LAH (76 mg, 2 mmol) was added. The resulting mixture was heated to reflux for 2 h and then cooled to 5° C., quenched with one drop of water. The precipitate formed was removed by filtration. The filtrate was diluted with 1N aqueous NaOH and extracted with EA. The organic layer was washed with brine and dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by prep-HPLC to give compound 2 as a yellow solid (20 mg, 13% yield). 1H-NMR (400 MHz, CDCl3) δ 8.00 (dd, 1H, J=8.0, 2.0 Hz), 7.44 (m, 1H), 7.19-7.00 (m, 8H), 6.87-6.81 (m, 3H), 5.30 (d, J=17.6 Hz, 1H), 4.59-4.55 (m, 2H), 4.29 (m, 1H), 3.72 (s, 3H), 3.45 (d, J=12.4 Hz, 1H), 2.62 (dd, J=13.2, 10.4 Hz, 1H), 2.49-2.39 (m, 3H), 2.24 (s, 3H). MS (ESI+) m/z: 437 [M+H]+

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 h
  3. customquenched with one drop of water
  4. customThe precipitate formed
  5. customwas removed by filtration
  6. additionThe filtrate was diluted with 1N aqueous NaOH
  7. extractionextracted with EA
  8. washThe organic layer was washed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-e455e07dff2147bd8be73da1727c87dc
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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