Nitrogen → cis-Tert-butyl 3-azido-4-fluoropyrrolidine-1-carboxylate
Reaction equation
N#N.[N:3]([C@H:6]1[C@H:10](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:9][N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:7]1)=[N+:4]=[N-:5].C1COCC1.[F-:34].C([N+](CCCC)(CCCC)CCCC)CCC>>[N:3]([C@H:6]1[C@@H:10]([F:34])[CH2:9][N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:7]1)=[N+:4]=[N-:5]Participants
5
Procedure
In a flame dried round-bottomed flask equipped with a magnetic stir bar, a reflux condenser, and under inert atmosphere (N2), a solution of trans-tert-butyl 3-azido-4-(tosyloxy)pyrrolidine-1-carboxylate (438 mg, 1.15 mmol) in 1M tetra-n-butyl-ammonium fluoride solution in THF (7.00 mL, 7.00 mmol) was stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and the residue was extracted with CH2Cl2, washed with water, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by FC (Hept/EA, 9:1→7:3) to afford cis-tert-butyl 3-azido-4-fluoropyrrolidine-1-carboxylate as a colorless oil. TLC: rf (Hept/EA, 7:3)=0.33. LC-MS-conditions 08: tR=0.81 min; [M-CH3+H]+=216.15.
Workup
- customIn a flame dried round-bottomed flask equipped with a magnetic stir bar, a reflux condenser
- temperatureat reflux overnight
- concentrationThe reaction mixture was concentrated under reduced pressure
- extractionthe residue was extracted with CH2Cl2
- washwashed with water
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by FC (Hept/EA, 9:1→7:3)
Sources & evidence
- ORD record
- ord-1111266051db4a769208573b3d90e358
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139524B2
Reaction notes
Loading…