Water → rel-(3aR,6aS)-Octahydro-2-(phenylmethyl)pyrrolo(3,4-c)pyrrole

Participants

Reaction Conditions

Reaction Steps

3-Benzyl-3,7-diazabicyclo[3.3.0]octan-2,4-dione hydrochloride (73.8 g, 275 mmol; from step (b) above) was added in portions to a suspension of LiAlH4 (83.5 g, 2.26 mol) in THF at 0° C. The reaction was slowly warmed to reflux. After refluxing for 16 h the reaction was cooled to 0° C. To the cold reaction there was added dropwise sequentially H2O (84 mL), 3 M NaOH (84 mL) and H2O (250 mL). The reaction was then stirred for an additional 15 minutes and filtered through a pad of Celite® to remove the inorganic salts. The filtrate was concentrated in vacuo to afford the crude product. Kugelrohr distillation (95–115° C./66.5 Pa (0.5 mm Hg)) provided 46.8 g (84%) of the sub-title compound as a colourless oil.

Provenance & Evidence