Aluminium lithium hydride → HCID 22981282, compound

HRID 1875463Notes

Reaction equation

HRID 1875463 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10](C(OC(C)(C)C)=O)[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:6][C:5]=1[Cl:25].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:25][C:5]1[CH:6]=[C:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:8]=[CH:9][C:4]=1[CH2:3][OH:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67351826HCID 67351826, compound

Product 1

HCID 22981282HCID 22981282, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of methyl-2-chloro-4-(bis-Boc-amino)-benzoate (491 mg) in THF (4 mL) was added lithium aluminum hydride (1.27 mL, 2M in THF), dropwise, the reaction mixture was stirred for 30 min and quenched with MeOH. The reaction mixture was diluted with EtOAc, the organic layer washed with saturated NH4Cl (1×), brine (1×), dried over Na2SO4 and volatiles removed. The residue was purified by column chromatography using 0-60% EtOAc/Hexanes to provide compound 2-chloro-4-(boc-amino)-benzylalcohol as a clear syrup (259 mg).

Workup

  1. customquenched with MeOH
  2. additionThe reaction mixture was diluted with EtOAc
  3. washthe organic layer washed with saturated NH4Cl (1×), brine (1×)
  4. dry with materialdried over Na2SO4 and volatiles
  5. customremoved
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bbb61a561cf8448e8d0b25e9acf333c5
Source dataset
uspto-grants-2012_11
Patent number
US08309554B2

Reaction notes

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