Aluminium lithium hydride → HCID 59900560, compound

HRID 567865Notes

Reaction equation

HRID 567865 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([N:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[C:18]([NH2:20])=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>O1CCCC1>[CH:7]1([N:13]2[CH2:17][CH2:16][CH2:15][C@@H:14]2[CH2:18][NH2:20])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54476888HCID 54476888, compound

Product 1

HCID 59900560HCID 59900560, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (7.3 ml, 1M in tetrahydrofuran, 7.3 mmol) was added dropwise to a solution of (2R)-1-cyclohexyl-2-pyrrolidinecarboxamide (preparation 147) (950 mg, 4.85 mmol) in tetrahydrofuran (15 ml) and once addition was complete, the reaction was heated under reflux for 20 hrs. The cooled mixture was carefully quenched with water, and extracted with ethyl acetate. The combined organic extracts were then dried over MgSO4 and evaporated under reduced pressure. The residue was suspended in dichloromethane, filtered through Whatman® fibre and the filtrate evaporated under reduced pressure to give the desired product as an oil (849 mg, 96%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureunder reflux for 20 hrs
  3. customThe cooled mixture was carefully quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were then dried over MgSO4
  6. customevaporated under reduced pressure
  7. filtrationfiltered through Whatman® fibre
  8. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-715212d5e56b434991e91c440c27f3f1
Source dataset
uspto-grants-2001_01
Patent number
US06180627B2

Reaction notes

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