Pyridine → Phenyl cyclopentylcarbamate

Cyclopentylamine (9.9 ml, 100 mmol) was dissolved in tetrahydrofuran (400 ml); pyridine (8.9 ml, 110 mmol) was added thereto; and the reaction mixture was stirred. The reaction mixture was cooled with ice; phenyl chloroformate (13.8 ml, 110 mmol) was added dropwise for 5 minutes while stirring; and the reaction mixture was stirred at room temperature for 24.5 hours. The reaction mixture was partitioned between ethyl acetate and water; and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained crystals were suspended in a solvent mixture of hexane:ethyl acetate=5:1, filtered off, washed with hexane, and dried under aeration to yield the title compound as colorless crystals (16.6 g, 81 mmol, 81%).

1. temperatureThe reaction mixture was cooled with ice
2. stirringwhile stirring
3. stirringand the reaction mixture was stirred at room temperature for 24.5 hours
4. customThe reaction mixture was partitioned between ethyl acetate and water
5. washand the organic layer was washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. additionThe obtained crystals were suspended in a solvent mixture of hexane
9. filtrationethyl acetate=5:1, filtered off
10. washwashed with hexane
11. customdried under aeration

ORD record

ord-895ec5c445a94c6aa0360997937a2f98

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468380B2