反应详情

Dissolve (S)-1,4-dibenzyl-2-vinylpiperazine (16.2 g, 55.5 mmol) in tetrahydrofuran (370 mL), add 9-BBN (0.56 L of a 0.5 M solution in tetrahydrofuran) via addition funnel, stir at room temperature overnight. Cool to 0° C. and treat with 30% aqueous hydrogen peroxide (195 mL), followed by 3N aqueous sodium hydroxide (195 mL). Allow to reach room temperature and stir for 24 h. Pour into separatory funnel, separate organic layer and remove solvent in vacuo. Take up residue in dichloromethane, add water and recombine with aqueous layer from before. Pour into separatory funnel, separate organic layer and extract aqueous layer with several portions of dichloromethane. Combine all organic layers, remove solvent in vacuo. Take up residue in 1 L of methanol, add 185 g of SCX resin. Filter slurry through Büchner funnel, washing well with methanol. To elute product, wash cake thoroughly with 50% 7N ammonia-methanol in dichloromethane. Concentrate filtrate in vacuo to obtain the title compound (16.6 g, 96%) as a thick brownish oil: mass spectrum (APCI): m/z=311.2 (M+1).

1. additionvia addition funnel
2. temperatureCool to 0° C.
3. customto reach room temperature
4. stirringstir for 24 h
5. additionPour into separatory funnel
6. customseparate organic layer
7. customremove solvent in vacuo
8. additionadd water and recombine with aqueous layer from before
9. additionPour into separatory funnel
10. customseparate organic layer
11. extractionextract aqueous layer with several portions of dichloromethane
12. customCombine all organic layers, remove solvent in vacuo
13. additionadd 185 g of SCX resin
14. filtrationFilter slurry through Büchner funnel
15. washwashing well with methanol
16. washTo elute product
17. washwash cake thoroughly with 50% 7N ammonia-methanol in dichloromethane