Aluminium lithium hydride → HCID 86744626, compound

HRID 982118Notes

Reaction equation

HRID 982118 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([CH2:10][C@H:11]1[C:16]2[C:17]([CH3:23])=[CH:18][CH:19]=[C:20]([O:21][CH3:22])[C:15]=2[CH2:14][C@@H:13]([CH2:24][N:25]=[N+]=[N-])[O:12]1)=[N+]=[N-]>C(OCC)C>[NH2:7][CH2:10][C@H:11]1[C:16]2[C:17]([CH3:23])=[CH:18][CH:19]=[C:20]([O:21][CH3:22])[C:15]=2[CH2:14][C@@H:13]([CH2:24][NH2:25])[O:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 56997872HCID 56997872, compound

Product 1

HCID 86744626HCID 86744626, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (2.4 mL of a 1.0 M solution in diethyl ether, 2.4 mmol) is added dropwise to a solution of [1R,3S] 1,3-bis(azidomethyl)-3,4-dihydro-5-methoxy-8-methyl-1H-2-benzopyran (283 mg, 1.2 mmol), from Step 5, in 10 mL of anhydrous diethyl ether at 0° C. The reaction mixture is allowed to warm to ambient temperature and stirred for 45 min. The reaction is then quenched by the sequential addition of 91 μL of water, 91 μL of 15% aqueous sodium hydroxide solution and 273 μL of water. The solution is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give the title compound.

Workup

  1. customThe reaction is then quenched by the sequential addition of 91 μL of water, 91 μL of 15% aqueous sodium hydroxide solution and 273 μL of water
  2. dry with materialThe solution is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-330caaa672ca44bbad5b148214c29a97
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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