Nitrogen → HCID 131733501, compound

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of trans-tert-butyl 3-azido-4-hydroxypyrrolidine-1-carboxylate (J. Med. Chem. 2010, 53, 6730-6746) (320 mg, 1.40 mmol) in pyridine (3 mL) was added TsCl (588 mg, 3.00 mmol). The mixture was stirred at 5° C. overnight. The solvent was removed under reduced pressure and the mixture was partitioned between CH2Cl2 and 10% aq. NaHCO3. The organic layer was washed with water, dried over MgSO4, and the solvent removed under reduced pressure. The residue was purified by FC (Hept/EA, 9.5:0.5→8:2) to afford trans-tert-butyl 3-azido-4-(tosyloxy)pyrrolidine-1-carboxylate as a colorless oil. LC-MS-conditions 08: tR=0.96 min; [M-CH3+H]+=368.10. TLC: rf (Hept/EA, 8:2)=0.22.

Provenance & Evidence