반응 #6058

반응 방정식

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

ammonium formate

→

title compound

수율 184.5%

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

수율 184.5%

용매

methanol

반응 조건

후처리

1. 1
   여과The reaction mixture was filtered
2. 2
   농축the filtrate concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 200 mL of diethyl ether
4. 4
   세척the ether solution was washed with 100 mL of 5% aqueous sodium bicarbonate solution
5. 5
   건조dried over anhydrous magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure

실험 절차

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).

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