Aluminium lithium hydride → HCID 21355906, compound

HRID 1870665Notes

Reaction equation

HRID 1870665 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C@@H:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@H:9]([CH3:13])[C:10]([NH2:12])=O>O1CCCC1>[CH3:13][C@@H:9]([C@H:8]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:7])[CH2:10][NH2:12]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54300456HCID 54300456, compound

Product 1

HCID 21355906HCID 21355906, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (2.3 g, 60.60 mmol) was added in portions to a stirring solution of (2S,3R)-3-amino-2-methyl-3-phenylpropionamide (2.6 g, 14.59 mmol) in tetrahydrofuran (54 ml) at ice-bath temperature. After 45 min, the mixture was heated at reflux for 16 h. With ice-bath cooling, the reaction was quenched by the portionwise addition of sodium sulfate decahydrate and some methanol until hydrogen evolution ceased. The solids were removed by filtration and washed with dichloromethane. The combined filtrates were evaporated to provide the title compound. MS (m/z): 165.2 (M+H)+ ; C10H16N2 requir. 164.3.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperatureWith ice-bath cooling
  4. customthe reaction was quenched by the portionwise addition of sodium sulfate decahydrate
  5. customThe solids were removed by filtration
  6. washwashed with dichloromethane
  7. customThe combined filtrates were evaporated

Sources & evidence

ORD record
ord-5ca449ec57c048939c40999473582fb0
Source dataset
uspto-grants-2000_08
Patent number
US06096753

Reaction notes

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