Triethylamine → 3-Azido-1-benzhydrylazetidine

温度

-10 °C

1-(diphenylmethyl)-3-hydroxyazetidine (5.5 g, 22.98 mmol) was dissolved in acetonitrile (16.5 mL), triethylamine (3.48 g, 34.45 mmol) was added. The reaction mixture was cooled to −10° C., methylsulfonyl chloride (3.16 g, 27.59 mmol) was added dropwise slowly. After completion of dropwise addition, the reaction was performed at 0° C. for 1 h, The resultant reaction liquid was poured into water, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, the filtrate was rotatedly concentrated to dryness to yield a white solid. The resultant white solid was added to N,N-dimethyl formamide (25 mL), sodium azide (5.38 g, 82.73 mmol) was added. The reaction mixture was warmed to 100° C. and the reaction was performed overnight. The resultant reaction liquid was cooled to room temperature, poured into water, extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered; the filtrate was rotatedly concentrated to dryness to yield 1-(diphenylmethyl)-3-azidoazetidine.

1. additionAfter completion of dropwise addition
2. customThe resultant reaction liquid
3. extractionextracted with ethyl acetate
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationthe filtrate was rotatedly concentrated to dryness
7. customto yield a white solid
8. additionwas added
9. temperatureThe reaction mixture was warmed to 100° C.
10. waitthe reaction was performed overnight
11. customThe resultant reaction liquid
12. temperaturewas cooled to room temperature
13. extractionextracted with dichloromethane
14. washThe organic phase was washed with water
15. dry with materialdried over anhydrous sodium sulfate
16. filtrationfiltered
17. concentrationthe filtrate was rotatedly concentrated to dryness

ORDレコード

ord-ec625a3dc1df4b6ea7157684c11f7365

出典データセット

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08952002B2