Aluminium lithium hydride → HCID 67001538, compound

HRID 2279230Notes

Reaction equation

HRID 2279230 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[F:7][C:8]1[CH:31]=[CH:30][C:11]([C:12]([N:14]2[CH2:29][CH2:28][N:17]3[C:18]4[N:27]=[CH:26][CH:25]=[CH:24][C:19]=4[NH:20][C:21](=O)[CH2:22][CH:16]3[CH2:15]2)=O)=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:31]=[CH:30][C:11]([CH2:12][N:14]2[CH2:29][CH2:28][N:17]3[C:18]4[N:27]=[CH:26][CH:25]=[CH:24][C:19]=4[NH:20][CH2:21][CH2:22][CH:16]3[CH2:15]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67001644HCID 67001644, compound

Product 1

HCID 67001538HCID 67001538, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid LiAlH4 (357 mg, 9.41 mmol) was added to a vigorously stirred solution of the product of Example 64B (528 mg, 1.55 mmol) in tetrahydrofuran (40 mL). The resulting gray suspension was heated at reflux under nitrogen for 1 hour and then cooled in ice. The reaction was quenched by successive addition of ethyl acetate (5 mL), water (0.35 ml), 15% NaOH (0.35 mL) and water (1.05 mL). The resulting slurry was stirred for 10 minutes, filtered (tetrahydrofuran (15 mL) and ethyl acetate (15 mL) rinse), and the filtrate was concentrated to provide the title compound, sufficiently pure for use in the next step: 1H NMR (300 MHz, CDCl3) δ ppm 1.78-1.90 (m, 1H), 1.92-2.03 (m, 1H), 2.19-2.31 (m, 1H), 2.44-2.62 (m, J=8.7 Hz, 2H), 2.72-2.85 (m, J=10.7 Hz, 1H), 3.26 (ddd, J=12.1, 5.6, 3.8 Hz, 1H), 3.38-3.62 (m, 6H), 6.67 (dd, J=7.5, 4.5 Hz, 1H), 6.74 (dd, J=7.5, 2.0 Hz, 1H), 6.94-7.06 (m, 2H), 7.28-7.39 (m, 2H), 7.78 (dd, J=4.8, 1.6 Hz, 1H); MS (ESI) m/z 313 (M+H)+.

Workup

  1. temperatureThe resulting gray suspension was heated
  2. temperatureat reflux under nitrogen for 1 hour
  3. temperaturecooled in ice
  4. customThe reaction was quenched by successive addition of ethyl acetate (5 mL), water (0.35 ml), 15% NaOH (0.35 mL) and water (1.05 mL)
  5. filtrationfiltered
  6. wash(tetrahydrofuran (15 mL) and ethyl acetate (15 mL) rinse)
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f78ed51d929c470dba7044ac4ed4ecdf
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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