Acetic Anhydride → (1R,4S)-1-acetylamino-4-(hydroxymethyl)-2-cyclopentene

温度

80 °C

25 g (1R,4S)-1-amino-4-(hydroxymethyl)-2-cyclopentene hydrochloride were dissolved in 182 ml of acetic anhydride, and at 0° C., a solution of 18.25 g of triethylamine in 60 ml of acetic anhydride were added thereto. The mixture was stirred at 80° C. for 3 h, then cooled to room temperature. The triethylamine hydrochloride was filtered off and washed with 120 ml of n-hexane. The filtrate was evaporated. 300 ml of toluene were added to the residue, and the mixture was stirred at room temperature in the presence of 5.2 g of activated carbon and 13 g of Celite for 20 min. The mixture was then filtered, and the filter cake was washed (3×40 ml of toluene), and the solvent was completely evaporated. 180 ml of methanol and 15.5 g of K2CO3 were added to the residue, and the mixture was stirred at room temperature for 10 h. The suspension was filtered off and the filtrate evaporated. The residue was suspended in 750 ml of isopropyl acetate and boiled in the presence of 0.5 g of activated carbon to reflux for 1.5 h. Following filtration of the activated carbon (70-80° C.), the filtrate was cooled at 0° C. overnight. The title compound was filtered, washed with 80 ml of cold isopropyl acetate and dried under reduced pressure to give 17.2 g of product. The yield was 66%.

1. temperaturecooled to room temperature
2. filtrationThe triethylamine hydrochloride was filtered off
3. washwashed with 120 ml of n-hexane
4. customThe filtrate was evaporated
5. addition300 ml of toluene were added to the residue
6. stirringthe mixture was stirred at room temperature in the presence of 5.2 g of activated carbon and 13 g of Celite for 20 min
7. filtrationThe mixture was then filtered
8. washthe filter cake was washed (3×40 ml of toluene)
9. customthe solvent was completely evaporated
10. addition180 ml of methanol and 15.5 g of K2CO3 were added to the residue
11. stirringthe mixture was stirred at room temperature for 10 h
12. filtrationThe suspension was filtered off
13. customthe filtrate evaporated
14. temperatureto reflux for 1.5 h
15. filtrationfiltration of the activated carbon (70-80° C.)
16. temperaturethe filtrate was cooled at 0° C. overnight
17. filtrationThe title compound was filtered
18. washwashed with 80 ml of cold isopropyl acetate
19. customdried under reduced pressure

ORDレコード

ord-30ebd1f378764aeb961435ec5797e90d

出典データセット

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07338945B2