Acetylene → Rac-tert-butyl (3r,4r)-3-hydroxy-4-(1h-1,2,3-triazol-1-yl)pyrrolidine-1-carboxylate
Reaktionsgleichung
[OH:1][C@H:2]1[C@H:6]([N:7]=[N+:8]=[N-:9])[CH2:5][N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:3]1.[CH:17]#[CH:18]>CC(C)=O>[OH:1][C@H:2]1[C@H:6]([N:7]2[CH:18]=[CH:17][N:9]=[N:8]2)[CH2:5][N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:3]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of trans 3-hydroxy-4-azido-1-N-(tert.-butoxy carbonyl)pyrrolidine (3.8 g, 17 mmol) in dry acetone (50 ml) was heated at 75°-80° C. for 40 hrs. After releasing the excess of acetylene, the reaction mixture was concentrated and the residue was purified on silica gel using ethyl acetate as eluant. Yield 3.66 g (87%) m.p. 91-93° C.; 1H NMR (CDCl3) δ: 1.46 (S, 9H), 3.25-4.25 (m, 5H), 4.83 (m, 1H), 7.63 (S, 1H), 7.70 (S, 1H).