Aluminium lithium hydride → HCID 18388025, compound

HRID 2391956Notes

Reaction equation

HRID 2391956 reaction equation
[CH3:1][C:2]([CH3:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C@@H:3]([C:5](OC)=[O:6])[NH2:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:4][CH:3]([C:2]([CH3:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:1])[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67065476HCID 67065476, compound

Product 1

HCID 18388025HCID 18388025, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of methyl beta,beta-dimethylphenylalaninate (1.4 g, 6.76 mmol) in THF (20 mL) at 0° C. was added dropwise a solution of lithium aluminum hydride (384 mg, 10.1 mmol) in THF (10 mL). After warming to 25° C. over 12 h, the solution was quenched by sequential addition of H2O (659 uL), 6N NaOH (500 uL) and H2O (2.4 mL). The resulting precipitate was filtered and the pad washed thoroughly with DCM. The filtrate was concentrated and purified via column chromatography (silica, 2-5% MeOH in DCM (1% NH4OH)) yielding the title compound (770 mg, 64%): LCMS (ES) m/e 179 (M+H)+.

Workup

  1. customthe solution was quenched by sequential addition of H2O (659 uL), 6N NaOH (500 uL) and H2O (2.4 mL)
  2. filtrationThe resulting precipitate was filtered
  3. washthe pad washed thoroughly with DCM
  4. concentrationThe filtrate was concentrated
  5. custompurified via column chromatography (silica, 2-5% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-98d8601c413547fcbe9cc8478f4b51b2
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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