Aluminium lithium hydride → HCID 86596610, compound

HRID 1865731Notes

Reaction equation

HRID 1865731 reaction equation
[CH3:1][N:2]([C@H:10]([C:20](N1CCOCC1)=[O:21])[C:11]([CH3:19])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:12])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:20]([C@@H:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6])[C:11]([CH3:19])([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH3:12])=[O:21]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69019789HCID 69019789, compound

Product 1

HCID 86596610HCID 86596610, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled solution (0° C., ice bath) of tert-butyl methyl[(1S)-2-methyl-1-(4-morpholinylcarbonyl)-2-phenylpropyl]carbamate (0.870 g, 2.32 mmol, from Reference Example 18) in anhydrous tetrahydrofuran (3.0 ml), 1.0M lithium aluminum hydride (5.8 ml, 5.8 mmol) in tetrahydrofuran is added dropwise over 30 minutes. The reaction mixture stirred at room temperature for 30 minutes and is quenched with 5% potassium hydrogen sulfate and stirred at room temperature for 15 minutes. The mixture is washed with ether (3 times). The organic layer is then collected and dried with sodium sulfate and concentrated in vacuo to give a colorless oil. The crude product is used without further purification. (0.940 g, 80%) MS [M+H] 292.2

Workup

  1. customis quenched with 5% potassium hydrogen sulfate
  2. stirringstirred at room temperature for 15 minutes
  3. washThe mixture is washed with ether (3 times)
  4. customThe organic layer is then collected
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give a colorless oil
  8. customThe crude product is used without further purification

Sources & evidence

ORD record
ord-2f5631f4d62a4fc0b8df803707226650
Source dataset
uspto-grants-2009_12
Patent number
US07626023B2

Reaction notes

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