反应详情

Triphenylphosphine (14.3 g) was added to a THF (190 ml) solution containing tert-butyl ((1S,2S)-2-hydroxycyclohexyl)carbamate (10.0 g), followed by ice cooling. Diethyl azodicarboxylate (40% in toluene) (24.3 g) and DPPA (15.3 g) were added dropwise to the reaction solution, followed by stirring at room temperature for 1 hour. The reaction solution was left overnight. The solvent was distilled away under reduced pressure. Water was added and then a 20% sodium hydroxide aqueous solution was added. Then, the organic layers were collected. Water (30 ml) was added to the obtained organic layers, followed by heating to 60° C. A THF (40 ml) solution containing triphenylphosphine (14.3 g) was added dropwise, followed by reflux for 2.5 hours. The solvent was distilled away under ordinary pressure. Toluene was added and the pH was adjusted with 3M hydrochloric acid to pH=1 or less. Then, the resulting aqueous layers were collected, ethyl acetate was added, and the pH was adjusted with a 20% sodium hydroxide aqueous solution to pH 12. The organic layers were collected and dried over anhydrous sodium sulfate. Light yellow oily matter of tert-butyl ((1S,2R)-2-aminocyclohexyl)carbamate (5.24 g) was thus obtained.

1. waitThe reaction solution was left overnight
2. distillationThe solvent was distilled away under reduced pressure
3. additionWater was added
4. additiona 20% sodium hydroxide aqueous solution was added
5. customThen, the organic layers were collected
6. additionWater (30 ml) was added to the obtained organic layers
7. temperatureby heating to 60° C
8. additionA THF (40 ml) solution containing triphenylphosphine (14.3 g)
9. additionwas added dropwise
10. temperatureby reflux for 2.5 hours
11. distillationThe solvent was distilled away under ordinary pressure
12. additionToluene was added
13. customThen, the resulting aqueous layers were collected
14. additionethyl acetate was added
15. customThe organic layers were collected
16. dry with materialdried over anhydrous sodium sulfate