Methyl iodide → (R)-Benzyl 3-((tert-butoxycarbonyl)(methyl)amino)pyrrolidine-1-carboxylate

Benzyl chloroformate (0.749 mL, 5.25 mmol) was added to a solution of tert-butyl(3R)-pyrrolidin-3-ylcarbamate (0.93 g, 5.0 mmol, TCI, Cat. No. A1171) and triethylamine (1.39 mL, 10.0 mmol) in methylene chloride (15.0 mL) at 0° C. The mixture was stirred at r.t. for 1 h. The mixture was diluted with CH2Cl2, washed with 0.5 N aqueous HCl, water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in N,N-dimethylformamide (10.0 mL), and cooled with ice-water. To the solution was added sodium hydride (0.300 g, 7.50 mmol) in small portions. The mixture was stirred for 15 min at r.t., and then methyl iodide (1.42 g, 10.0 mmol) was added. The mixture was stirred for additional 30 min., then diluted with ether, washed with water and brine, over Na2SO4, filtered, and concentrated under reduced pressure to give the desired product which was directly used in the next step reaction without further purification. LCMS (M+Na)+: m/z=357.3.

1. customat 0° C
2. washwashed with 0.5 N aqueous HCl, water and brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in N,N-dimethylformamide (10.0 mL)
7. temperaturecooled with ice-water
8. stirringThe mixture was stirred for 15 min at r.t.
9. stirringThe mixture was stirred for additional 30 min.
10. washwashed with water and brine, over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure

ORD record

ord-0a9058fe00454c56b8975ddfae2e1629

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436008B2