Methanol → HCID 23087144, compound

Temperature

80 °C

By referring to the synthetic method of J. Org. Chem., 1984, 49, 2081, to a solution of 1-benzyl-3-(4-methoxy-2-nitrophenyl)pyrrolidine (647 mg) in 1,2-dichloroethane (15 ml) was added chloroformic acid 1-chloroethyl ester (0.33 ml) on an ice bath, the solution was stirred for 2 hours at 80° C., and then stirred for 2.5 hours at 100° C. Methanol (5 ml) was added thereto, the solution was stirred for 3 hours at 80° C., then triethylamine (1 ml) and di-tert-butyl dicarbonate (0.7 ml) were sequentially added thereto on an ice bath, and the solution was stirred for 40 minutes at room temperature. Water was added thereto followed by stirring. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. Obtained by purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), 3-(4-methoxy-2-nitrophenyl)pyrrolidine-1-carboxylic acid tert-butyl ester (436 mg) was dissolved in trifluoroacetic acid (2 ml), the solution was stirred for 1 hour at room temperature, and neutralized with ammonia solution. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo to provide the title compound (207 mg).

1. stirringstirred for 2.5 hours at 100° C
2. stirringthe solution was stirred for 3 hours at 80° C.
3. stirringon an ice bath, and the solution was stirred for 40 minutes at room temperature
4. stirringby stirring
5. extractionThe solution was extracted with ethyl acetate
6. washsequentially washed with water and brine
7. dry with materialdried over anhydrous magnesium sulfate
8. customthe solvent was evaporated in vacuo
9. customObtained
10. customby purifying the residue by silica gel column chromatography (hexane-ethyl acetate system), 3-(4-methoxy-2-nitrophenyl)pyrrolidine-1-carboxylic acid tert-butyl ester (436 mg)
11. dissolutionwas dissolved in trifluoroacetic acid (2 ml)
12. stirringthe solution was stirred for 1 hour at room temperature
13. extractionThe solution was extracted with ethyl acetate
14. washsequentially washed with water and brine
15. dry with materialdried over anhydrous magnesium sulfate
16. customthe solvent was evaporated in vacuo

ORD record

ord-697cc452603e4975af244d00900ea59f

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960412B2