With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.31970-04-4,Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate,as a common compound, the synthetic route is as follows.
Example 1.3: Benzyl 3,4-epoxypyrrolidine-i-carboxylate (5); NBS (5.47 g, 31 mmol) is added to a solution of olefin 4 (5.02 g, 25 mmol) in DMSO (65 mL) and water (3.4 mL) at 0 0C. The reaction mixture is warmed to room temperature, stirred for 1.5 h then further NBS (1.1 g, 6.2 mmol) is added. After stirring for a further 3.5 h the reaction is quenched by the addition of water (150 mL) then extracted into EtOAc (3 x 150 mL). The combined organic phase is washed with brine (3 x 100 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue is dissolved in MeOH (80 mL), cooled to 0 0C and then an aqueous solution of NaOH (37 mL, 37 mmol, 1 M) is added in one portion. The reaction is warmed to room temperature, stirred for 5 h then the MeOH is removed under reduced pressure. The residue is diluted with water (100 mL) and extracted into EtOAc (3 x 200 mL). The combined organic phase is washed with brine (200 mL), dried (MgSO4), filtered and concentrated under reduced pressure. Flash chromatography of the residue (3 : 7 then 4 : 6, EtOAc: Petrol) affords the title compound as a pale yellow oil (3.69 g, 68% over the 2 steps). 13C NMR (125 MHz, CDCI3): delta = 155.3, 136.6, 128.5, 128.0, 127.9, 67.0, 55.5, 54.9, 47.5 and 47.2 ppm; MS (ESI): 242 ([MNa]+, 100%); HRMS (ESI): found: 242.0791 , C12H13NO3Na ([MNa]+) requires: 242.0793. (Tetrahedron: Asymmetry, 2006, 17, 2876-2883).
31970-04-4, 31970-04-4 Benzyl 2,5-dihydro-1H-pyrrole-1-carboxylate 643471, apyrrolines compound, is more and more widely used in various fields.
Reference£º
Patent; ALBERT EINSTEIN COLLEGE OF YESHIVA UNIVERSITY; INDUSTRIAL RESEARCH LIMITED; EVANS, Gary Brian; LONGSHAW, Alistair Ian; SCHRAMM, Vern L.; TYLER, Peter, Charles; WO2011/8110; (2011); A1;,
Pyrroline – Wikipedia
1-Pyrroline | C4H7N – PubChem