Aluminium lithium hydride → HCID 67001448, compound

HRID 2279219Notes

Reaction equation

HRID 2279219 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[CH2:23][CH2:22][N:11]2[C:12]3[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=3[NH:14][C:15](=O)[CH2:16][CH:10]2[CH2:9]1>O1CCCC1>[CH3:7][N:8]1[CH2:23][CH2:22][N:11]2[C:12]3[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=3[NH:14][CH2:15][CH2:16][CH:10]2[CH2:9]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 49764679HCID 49764679, compound

Product 1

HCID 67001448HCID 67001448, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid LiAlH4 (100 mg, 2.63 mmol) was added to a stirred solution of the product of Example 22E (72 mg, 0.311 mmol) in tetrahydrofuran (10 mL) at room temperature. The resulting mixture was heated at reflux under nitrogen for 2 hours, then cooled in ice and quenched by successive addition of ethyl acetate (4 mL), water (0.1 mL), 15% NaOH (0.1 mL) and water (0.3 mL). The mixture was filtered through a pad of diatomaceous earth with an ethyl acetate (25 mL total) rinse. The filtrate was concentrated under vacuum to provide the title compound, sufficiently pure for use in the next step: 1H NMR (300 MHz, CDCl3) δ ppm 2.06-2.20 (m, 2H), 2.25-2.42 (m, 2H), 2.37 (s, 3H), 2.62 (d, J=9.5 Hz, 1H), 2.77-2.87 (m, 1H), 3.08 (dt, J=11.6, 3.1 Hz, 1H), 3.18 (ddd, J=12.2, 5.3, 2.8 Hz, 1H), 3.22-3.33 (m, 1H), 3.64-3.75 (m, 2H), 6.53 (dd, J=7.5, 2.0 Hz, 1H), 6.76 (td, J=7.4, 1.8 Hz, 1H), 6.83 (td, J=7.4, 1.8 Hz, 1H), 6.92 (dd, J=7.5, 1.6 Hz, 1H); MS (DCI) m/z 218 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux under nitrogen for 2 hours
  3. temperaturecooled in ice
  4. customquenched by successive addition of ethyl acetate (4 mL), water (0.1 mL), 15% NaOH (0.1 mL) and water (0.3 mL)
  5. filtrationThe mixture was filtered through a pad of diatomaceous earth with an ethyl acetate (25 mL total)
  6. washrinse
  7. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-ca6c81604e9a4745a64cde34cbb03325
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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