反应详情

Diisopropyl azodicarboxylate (1.19 g, 5.87 mmol) was added to an ice cooled mixture of tert-butyl (3R)-3-hydroxypyrrolidine-1-carboxylate (1 g, 5.34 mmol), phenol (0.5 g, 5.34 mmol) and triphenylphosphine (1.5 g, 5.8 mmol) in THF (14 mL). The mixture was stirred at room temperature for 20 h. The mixture was then concentrated under vacuum and the residue was twice triturated with diethyl ether. The resultant solid was filtered off and discarded. The filtrate was washed with 1M aq. sodium hydroxide, dried over sodium sulfate and concentrated. The residue was purified by FCC, eluting with 10% EtOAc in heptane to afford the title compound (0.893 g, 63%). Method B HPLC-MS: MH+ requires m/z=208 Found: m/z=208, Rt=2.20 min (91%).

1. temperaturecooled
2. concentrationThe mixture was then concentrated under vacuum
3. customthe residue was twice triturated with diethyl ether
4. filtrationThe resultant solid was filtered off
5. washThe filtrate was washed with 1M aq. sodium hydroxide
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customThe residue was purified by FCC
9. washeluting with 10% EtOAc in heptane