Water → HCID 13772857, compound

HRID 978590Notes

Reaction equation

HRID 978590 reaction equation
O=[C:2]1[N:6]([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:8])[CH2:5][CH:4]([C:15](OC)=[O:16])[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:9]1([CH:7]([N:6]2[CH2:2][CH2:3][CH:4]([CH2:15][OH:16])[CH2:5]2)[CH3:8])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 13772851Methyl 5-oxo-1-(1-phenylethyl)-3-pyrrolidinecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 13772857HCID 13772857, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 10.0 g (40.5 mmol) [3R-(R*, R*)]methyl 5-oxo-1-(-1-phenylethyl)-3-pyrrolidinecarboxylate in 75 ml dry tetrahydrofuran was added dropwise to a mixture of 6.50 g (171 mmol) lithium aluminum hydride in 100 ml tetrahydrofuran. The mixture was refluxed overnight, diluted with 50 ml tetrahydrofuran and treated dropwise with 6.5 ml water, 6.5 ml 15% sodium hydroxide and 19.5 ml water. Solids were removed by filtration and the filtrate was evaporated to a syrup which was dissolved in dichloromethane, dried (MgSO4), and reevaporated to give 8.06 g of crude crystalline product. Recrystallization from hexane afforded 7.25 g (87%) of the title compound, mp 86°-88° C. [α]D +51.3° C. (C, 1.06, methanol).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customSolids were removed by filtration
  3. customthe filtrate was evaporated to a syrup which
  4. dissolutionwas dissolved in dichloromethane
  5. dry with materialdried (MgSO4)
  6. customreevaporated
  7. customto give 8.06 g of crude crystalline product
  8. customRecrystallization from hexane

Sources & evidence

ORD record
ord-161929efcf3b4f618bf4e7011dd5030c
Source dataset
uspto-grants-1987_05
Patent number
US04665079

Reaction notes

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