Triethylamine → HCID 58055039, compound

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.

1. extractionextracted with CHCl3
2. dry with materialThe extract was dried over Na2SO4
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in THF (5 mL)
5. additionTo the solution was added 10% palladium on activated carbon (20 mg)
6. stirringstirred at room temperature for 15 hours
7. customThe solution obtained by filtration through Celite
8. washwashing the filter cake with MeOH
9. concentrationwas concentrated in vacuo
10. dissolutionThe residue was dissolved in CHCl3 (3 mL)
11. temperaturerefluxed for 1 day
12. temperaturecooled to room temperature
13. customThe resulting mixture was purified with silica gel column chromatography (eluent: CHCl3/MeOH=99/1˜80/20)

ORD record

ord-d6b769f728ff4a7892e2f2358930bff5

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263632B2