Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate → Methyl 1-benzylpyrrolidine-3-carboxylate

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Reaction Steps

A solution of methyl 1-benzyl-2-oxo-4-pyrrolidylcarboxylate (D10, 35.4 g, 0.18 mole) in dry THF (135 ml) was added dropwise over 30 mins to IM borane-THF solution (228 ml, 0.23 mole) at 0° C. under nitrogen, and when addition was complete the solution was heated under reflux for 1 h. The solution was cooled to room temperature, then treated dropwise with 8% hydrogen chloride/methanol (114 ml, 0.25 mole HCl) and stirred for 18 h, followed by 3 h at reflux. The mixture was then concentrated in vacuo and the residue treated with water (40 ml), washed with ether (2×50 ml), basified with 40% sodium hydroxide solution, saturated with potassium carbonate and extracted with ether (3×70 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to leaye a yellow oil, which was purified by distillation (b.p. 146° C.0.7 mm) to give the title compound (D11) as a colourless oil (19.8 g, 50%).

Provenance & Evidence