反应详情

温度

80 °C

A solution of ethylisocyanate (0.038 ml, 0.48 mmol), triethylamine (0.065 ml) and cis-N-benzyl-N-[4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]amine (0.122 g) in dichloroethane (10 ml) was stirred at room temperature for 60 hr. The reaction mixture was partitioned between water (10 ml) and dichloromethane (10 ml). The aqueous layer was separated and extracted with dichloromethane (2×10 ml) and the combined organic extracts washed with brine (10 ml), dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting residue was dissolved in dichloromethane (15 ml) and warmed with a mixture of water (7.5 ml) and trifluoroacetic acid (7.5 ml) at 80° C. for 17 hr. Toluene (25 ml) was then added and the mixture concentrated in vacuo. Methanol (25 ml) was then added and the mixture again concentrated in vacuo. Purification via flash chromatography (SiO2, ethyl acetate/petroleum ether) afforded the title compound (0.016 g, 19%) as a colourless solid. δH (CD3OD) 1.08 (3H, t), 1.57-1.88 (6H, m), 2.12 (2H, m), 3.16 (1H, m), 3.24 (2H, m), 4.17 (1H, m), 4.52 (2H, s), 6.09 (1H, t), 6.24 (1H, dd), 6.29 (1H, d), 6.98 (1H, d) and 7.22-7.37 (5H, m). m/s(ES+) 369.54 (M+H)+.

1. customThe reaction mixture was partitioned between water (10 ml) and dichloromethane (10 ml)
2. customThe aqueous layer was separated
3. extractionextracted with dichloromethane (2×10 ml)
4. washthe combined organic extracts washed with brine (10 ml)
5. dry with materialdried over magnesium sulfate
6. filtrationfiltered
7. customevaporated in vacuo
8. dissolutionThe resulting residue was dissolved in dichloromethane (15 ml)
9. additionToluene (25 ml) was then added
10. concentrationthe mixture concentrated in vacuo
11. additionMethanol (25 ml) was then added
12. concentrationthe mixture again concentrated in vacuo
13. customPurification via flash chromatography (SiO2, ethyl acetate/petroleum ether)