Aluminium lithium hydride → HCID 21355906, compound

HRID 480433Notes

Reaction equation

HRID 480433 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)+; C10H16N2requir. 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-b2a962eb2c2a4969a60879b5f6d76077
Source dataset
uspto-grants-2003_11
Patent number
US06649604B2

Reaction notes

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