反応 #6058

反応方程式

((1,1-dimethylethyl)diphenylsilyloxy)-3-(((1,1-dimethylethyl)diphenyl-silyl)oxymethyl)-1-azidocyclobutane

ammonium formate

→

title compound

収率 184.5%

2-(((1,1-dimethylethyl)diphenylsilyl)oxy)-3-(((1,1-dimethylethyl)-diphenylsilyl)oxymethyl)-1-aminocyclobutane

収率 184.5%

溶媒

methanol

反応条件

後処理

1. 1
   ろ過The reaction mixture was filtered
2. 2
   濃縮the filtrate concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 200 mL of diethyl ether
4. 4
   洗浄the ether solution was washed with 100 mL of 5% aqueous sodium bicarbonate solution
5. 5
   乾燥dried over anhydrous magnesium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure

実験手順

2-(((1,1-dimethylethyl)diphenylsilyloxy)-3-(((1,1-dimethylethyl)diphenyl-silyl)oxymethyl)-1-azidocyclobutane (800 mg, 1.29 mmol), the product of Step M, was dissolved in 20 mL of methanol. To this solution was added 200 mg of 5% palladium on carbon, followed by 420 mg of ammonium formate. The flask was stoppered and the reaction mixture was stirred at ambient temperature for 23 h. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was dissolved in 200 mL of diethyl ether and the ether solution was washed with 100 mL of 5% aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 707 mg (92% yield) of the title compound; MS DCI-NH3M/Z: 594 (M+H)+ ; 1H NMR (CDCl3) δ 0.88-1.08 (m, 18H), 1.95-2.15 (m, 3H), 3.01 (q, 1H), 3.5 (m, 2H), 3.68 (t, 1H).

出典