Dimethylformamide → ((1S,2S,4R)-4-azido-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)methanol
反応式
CS(O[C@H:6]1[CH2:10][C@@H:9]([CH2:11][OH:12])[C@@H:8]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:7]1)(=O)=O.CN(C)C=O.[N-:26]=[N+:27]=[N-:28].[Na+]>>[N:26]([C@@H:6]1[CH2:10][C@@H:9]([CH2:11][OH:12])[C@@H:8]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:7]1)=[N+:27]=[N-:28]参加物
4
反応条件
- 温度
- 55 °C
実験手順
To a solution of (1S,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-(hydroxymethyl)-cyclopentyl methanesulfonate (0.470 g, 0.00145 mol) in N,N-Dimethylformamide (6 mL, 0.08 mol) was added sodium azide (0.4 g, 0.006 mol) 23° C., and the mixture was heated at 55° C. for 3 hours. The reaction was cooled to 23° C., quenched by addition of water and extracted with Et20 (3×), dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (10 to 25% ethyl acetate/hexane) to obtain 211 mg (53.7%).