Aluminium lithium hydride → HCID 86730142, compound

HRID 1850114Notes

Reaction equation

HRID 1850114 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]1[CH:20]=[CH:19][C:14]([C:15](OC)=[O:16])=[CH:13][CH:12]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOC(C)=O.CCCCCCC>C1COCC1>[OH:16][CH2:15][C:14]1[CH:13]=[CH:12][C:11]([C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:10])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21899848Ethylacetate heptaneHCID 57432297(S)-Methyl 4-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

Product 1

HCID 86730142HCID 86730142, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled (0° C.) solution of (S)-methyl 4-(1-(tert-butoxycarbonylamino)ethyl)benzoate (6.35 g, 22.7 mmol) in THF (114 mL) was added a solution of LAH in THF (2.0 M, 13.64 mL, 27.3 mmol) and the resulting mixture was stirred at room temperature for 40 min. The reaction mixture was quenched by addition of a 1N NaOH solution until gas evolution ceased. The reaction mixture was filtered, washed with EtOAc. After separation, the aqueous phase was washed with EtOAc (2×150 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/heptane 0 to 100%) provided (S)-tert-butyl 1-(4-(hydroxymethyl)phenyl)ethylcarbamate as a white solid (5.01 g, 84% yield).

Workup

  1. customThe reaction mixture was quenched by addition of a 1N NaOH solution until gas evolution
  2. filtrationThe reaction mixture was filtered
  3. washwashed with EtOAc
  4. customAfter separation
  5. washthe aqueous phase was washed with EtOAc (2×150 mL)
  6. dry with materialCombined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9e73f802cec84b6f9a9e5ff809fa0594
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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