Monobenzone → 2-(4-Benzyloxy-phenoxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

To a 15 mL of anhydrous DMF was added NaH (60% dispersion in oil, 338 mg, 8.44 mmol), and the resulting reaction mixture was cooled to 0° C. p-benzyloxy phenol (1.41 g, 7.03 mmol) was added and the reaction mixture was stirred at rt for 45 min. It was then cooled to −5° C., and (R)-Boc-prolinol tosylate (2.5 g, 7.03 mmol) in anhydrous DMF (5 mL) was cooled in a separate ice-bath and added dropwise to the reaction mixture. It was then allowed to warm to rt and stirred at 92° C. for 5 h and at rt overnight. The resulting mixture was poured into 200 mL ice/water and stirred for an hour. The resulting precipitate was filtered, washed with ether, dried over MgSO4, concentrated, recrystallized with ether/hexane to give shiny yellow crystals (1.5 g, 55%).

1. customthe resulting reaction mixture
2. additionwas added
3. temperatureIt was then cooled to −5° C.
4. additionadded dropwise to the reaction mixture
5. temperatureto warm to rt
6. stirringstirred at 92° C. for 5 h and at rt overnight
7. stirringstirred for an hour
8. filtrationThe resulting precipitate was filtered
9. washwashed with ether
10. dry with materialdried over MgSO4
11. concentrationconcentrated
12. customrecrystallized with ether/hexane

ORD record

ord-188a746988c84b5d953e1fe0403ef6ff

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728032B2