Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate → (1-Benzylpyrrolidin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

First, N-benzyl-pyrrolidine-3-methanol was prepared as follows. Methyl N-benzyl-5-oxo-pyrrolidine-3-carboxylate (11.66 g, 50 mmol) was dissolved in diethyl ether and cooled to 0° C. This solution was added to a 0° C. suspension of lithium aluminum hydride in diethyl ether under nitrogen atmosphere. After addition, the mixture was refluxed for 1 hr. and then cooled with an ice bath. To quench the reaction, sodium sulfate decahydrate was added and the mixture was stirred for 1 hr. After filtration, the filtrate was collected, and concentrated to dryness to give N-Benzyl-pyrrolidine-3-methanol. ESMS (C12H17NO): calcd. 191.13; obsd. 192–2 [M+H]+. Retention time (anal. HPLC: 10–70% MeCN/H2O over 5 min)=0.95 min.

Provenance & Evidence