Water → HCID 13772857, compound

HRID 1198601Notes

Reaction equation

HRID 1198601 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*)]-5-oxo-1-(-1-phenylethyl)-3 -pyrrolidinecarboxylic acid, methyl ester in 75 mL dry tetrahydrofuran was added dropwise to a mixture of 6.50 g (171 mmol) of lithium aluminum hydride in 100 mL of tetrahydrofuran. The mixture was refluxed overnight, diluted with 50 mL of tetrahydrofuran and treated dropwise successively 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-34898778ac17429297c476ccda7b3dfb
Source dataset
uspto-grants-1994_01
Patent number
US05281612

Reaction notes

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