(2S)-1-Triphenylmethyl-2-pyrrolidinecarboxylic acid methyl ester → HCID 21575548, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5.00 g (13.4 mmol) of the above ester in 50 mL of diethyl ether is added dropwise to a mixture of 0.509 g (13.4 mmol) of solid lithium aluminum hydride in 10 mL of ether while stirring under nitrogen. The mixture is brought to a gentle reflux and an additional 6.7 mL (6.7 mmol) of a 1M solution of lithium aluminum hydride in ether is injected by syringe. After refluxing for 2 hrs the reaction is cooled to 22° C. and quenched with 10 mL of methanol. The mixture is partitioned between 100 mL of 0.5M NaOH and 50 mL of ether and then stirred vigorously for 25 minutes and filtered. The ether layer is separated, washed with brine (30 mL), dried (MgSO4) and evaporated to give 4.20 g of (1-tritylpyrrolidin-2-yl)methanol as a white foam. By the method described in preparation 2, this material is used to prepare the title compound which is recrystallized from ethyl acetate/hexane.

Provenance & Evidence