Water → HCID 13772857, compound

Participants

Reaction Steps

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).

Provenance & Evidence