Aluminium lithium hydride → HCID 86744627, compound

HRID 982120Notes

Reaction equation

HRID 982120 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][OH:25])[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][OH:25])[O:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86744625HCID 86744625, compound2×

Product 1

HCID 86744627HCID 86744627, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Lithium aluminum hydride (1.1 mL of a 1.0M solution in diethyl ether, 1.1 mmol) is added dropwise to a solution of 289 mg (1.1 mmol) of [1R,3S] 1-azidomethyl-3,4-dihydro-3-hydroxymethyl-5-methoxy-8-methyl-1H-2-benzopyran, the product of Step 4 of Example 142, in 10 mL of anhydrous diethyl ether at 0° C. The reaction mixture is allowed to warm to ambient temperature and stirred for 40 min. The reaction mixture is cooled to 0° C. and quenched by the sequential addition of 42 μL of water, 42 μL of 15% aqueous sodium hydroxide solution and 126 μL of water. The solution is dried over anhydrous magnesium sulfate and filtered. The filtrate is concentrated in vacuo to give the title compound.

Workup

  1. customat 0° C
  2. temperatureThe reaction mixture is cooled to 0° C.
  3. customquenched by the sequential addition of 42 μL of water, 42 μL of 15% aqueous sodium hydroxide solution and 126 μL of water
  4. dry with materialThe solution is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-bb108cddabab46a8b313ad52986c30b1
Source dataset
uspto-grants-1991_02
Patent number
US04994486

Reaction notes

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