Triethylamine → HCID 58055039, compound

Participants

Reaction Steps

To the solution of tert-butyl (3R,4S)-3-(2-azidoethyl)-4-hydroxy-3-methoxypyrrolidine-1-carboxylate (85 mg) in CHCl3 (5 mL) was added triethylamine (140 mg) and MsCl (50 mg) at room temperature. And the mixture was stirred at room temperature for 1 hour. After the period, the mixture was poured into saturated aqueous solution of NaHCO3 and extracted with CHCl3. The extract was dried over Na2SO4 and concentrated. The residue was dissolved in THF (5 mL). To the solution was added 10% palladium on activated carbon (20 mg). The resulting solution was placed under a H2 atmosphere (balloon pressure) and stirred at room temperature for 15 hours. The solution obtained by filtration through Celite and washing the filter cake with MeOH was concentrated in vacuo. The residue was dissolved in CHCl3 (3 mL) and refluxed for 1 day and then cooled to room temperature. The resulting mixture was purified with silica gel column chromatography (eluent: CHCl3/MeOH=99/1˜80/20) to give tert-butyl (3aR,6aR)-3a-methoxyhexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate as a pale yellow foam.

Provenance & Evidence