Aluminium lithium hydride → HCID 54061615, compound

HRID 1992714Notes

Reaction equation

HRID 1992714 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[C:21](OC(C)(C)C)=O)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C@@H:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 55944529HCID 55944529, compound

Product 1

HCID 54061615HCID 54061615, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(S)-tert-butyl 2-(4-benzylpiperazine-1-carbonyl)pyrrolidine-1-carboxylate 1.01 g (2.71 mmol) in THF (10 ml) was added slowly to a solution of 1M lithium aluminum hydride in THF (8.2 ml) at 0° C. under argon protection. The reaction mixture was refluxed for 2 hours, cooled, quenched with water and extracted with ethyl ether 2×50 ml. The combined organic solution was washed with brine, dried over sodium sulfate and concentrated to give 0.71 g of desired product in 96% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. temperaturecooled
  3. customquenched with water
  4. extractionextracted with ethyl ether 2×50 ml
  5. washThe combined organic solution was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-265b8c2b736e479d9df9c90eab181508
Source dataset
uspto-grants-2010_01
Patent number
US07649092B2

Reaction notes

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