Aluminium lithium hydride → HCID 59900560, compound

HRID 2228801Notes

Reaction equation

HRID 2228801 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 aluminium 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-7a076d6ac44d43d6ac04d975df02d7a0
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

Loading…