Aluminium lithium hydride → HCID 11950913, compound

HRID 251445Notes

Reaction equation

HRID 251445 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][CH:8]([CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[C:9](O)=[O:10]>O1CCCC1>[NH2:7][CH:8]([CH2:12][CH2:13][N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1)[CH2:9][OH:10]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57459750HCID 57459750, compound

Product 1

HCID 11950913HCID 11950913, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
22 °C

Procedure

a solution of 1M lithium aluminium hydride (12.2 ml, 12.2 mmol) in tetrahydrofuran is added to a cold (−20° C.) suspension of 2-amino-4-pyrrolidin-1-ylbutanoic acid (0.994 g, 4.05 mmol) in tetrahydrofuran (20 ml). The mixture is left to warm to 22° C. and is then heated for one hour at 60° C. The mixture is then cooled to 0° C. and is carefully quenched by the successive addition of water, 1 N aqueous sodium hydroxide and water. After one hour stirring at 0° C., the suspension is filtered and the solid is washed with ethyl acetate. The liquid phase is concentrated in vacuo to yield 318 mg of 2-amino-4-pyrrolidin-1-ylbutan-1-ol ax35 as a yellow oil.

Workup

  1. waitThe mixture is left
  2. temperatureis then heated for one hour at 60° C
  3. temperatureThe mixture is then cooled to 0° C.
  4. customis carefully quenched by the successive addition of water, 1 N aqueous sodium hydroxide and water
  5. filtrationthe suspension is filtered
  6. washthe solid is washed with ethyl acetate
  7. concentrationThe liquid phase is concentrated in vacuo

Sources & evidence

ORD record
ord-2c1bb2fb577547429d22863f04f6e772
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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