Aluminium lithium hydride → (R)-2-Amino-2-ethylhexan-1-OL

HRID 342868Notes

Reaction equation

HRID 342868 reaction equation
[NH2:1][C:2]([CH2:9][CH3:10])([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][OH:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C@:2]([CH2:9][CH3:10])([CH2:5][CH2:6][CH2:7][CH3:8])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 534210662-Amino-2-ethylhexan-1-ol

Product 1

HCID 15406632(R)-2-Amino-2-ethylhexan-1-OLYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step (e) (20 g) was added to a 1M solution of lithium aluminium hydride (1.5 molar equivalents) in THF and the mixture reflexed for 3 hours, then stirred for 16 hours at room temperature. The mixture was cooled to about 0° C., then quenched with water and 1N aqu. NaOH added. The resulting solid was broken up with additional water and the suspension heated at 50° C. for 5 minutes, then cooled to room temperature, diethyl ether (100 ml) added and filtered. The filtrate was evaporated in vacuo to give the desired product as an oil (82% yield).

Workup

  1. temperatureThe mixture was cooled to about 0° C.
  2. customquenched with water and 1N aqu
  3. additionNaOH added
  4. temperaturethe suspension heated at 50° C. for 5 minutes
  5. temperaturecooled to room temperature
  6. additiondiethyl ether (100 ml) added
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-8499dbf9028e4886bc16ecab6d46f42e
Source dataset
uspto-grants-1999_01
Patent number
US05859240

Reaction notes

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