Aluminium lithium hydride → HCID 86594489, compound

HRID 1985935Notes

Reaction equation

HRID 1985935 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]([C@@H:10]([C@H:14]([CH2:20][CH3:21])[CH2:15][C:16]([F:19])([F:18])[F:17])[C:11](O)=[O:12])=[N+]=[N-]>C1COCC1>[NH2:7][C@@H:10]([C@H:14]([CH2:20][CH3:21])[CH2:15][C:16]([F:17])([F:18])[F:19])[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86594490HCID 86594490, compound

Product 1

HCID 86594489HCID 86594489, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a gray slurry of lithium aluminum hydride (LAH—110.6 mg, 2.91 mmol) in THF (2 mL) at 0° C. was added dropwise over 5 min (2S,3R)-2-azido-3-ethyl-5,5,5-trifluoropentanoic acid (130 mg, 583 mmol). The resulting slurry was allowed to warm to 25° C. for 19 h. The reaction was quenched by sequential addition of H2O (0.5 mL), 1N NaOH (1.5 mL) and H2O (0.5 mL) at 0° C. The white precipitate that formed after 5 h was filtered off, the organic solvent was dried over MgSO4, filtered and concentrated to obtain (2S,3R)-2-amino-3-ethyl-5,5,5-trifluoropentan-1-ol as a crude oil (120 mg, 96%). Mass Spectrum (+ESI): 186 (M+H)+.

Workup

  1. customThe reaction was quenched by sequential addition of H2O (0.5 mL), 1N NaOH (1.5 mL) and H2O (0.5 mL) at 0° C
  2. customThe white precipitate that formed after 5 h
  3. filtrationwas filtered off
  4. dry with materialthe organic solvent was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6dcaf1e5ebfb427891884c58e8f3b229
Source dataset
uspto-grants-2009_06
Patent number
US07547725B2

Reaction notes

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