반응 #1929088

반응 방정식

CH2Cl2

bisphosphonate

Tetraallyl Methylenebisphosphonate

NaH

DMF

→

aminobisphosphonate

수율 59.0%

Tetraallyl 1-aminomethylenebisphosphonate

수율 59.0%

용매

THF

반응 조건

후처리

1. 1
   온도cooled in a dry ice/acetone bath
2. 2
   workup.STIRRINGThe resulting mixture was stirred for 10 min at the same temperature
3. 3
   기타18 h
4. 4
   기타at room temperature
5. 5
   기타the solids were removed by filtration
6. 6
   세척washed with several portions of CH2Cl2
7. 7
   농축The combined filtrates were concentrated in vacuo
8. 8
   기타purified by flash chromatography on silica gel using a gradient of 0-5% MeOH/EtOAc

실험 절차

To a solution of bisphosphonate 23 (2.0 g, 5.95 mmol) in DMF (6 mL) was added NaH (60% dispersion in mineral oil, 254 mg, 6.35 mmol) portionwise. The solution was stirred for 45 min at room temperature and added to a solution of O-(diphenylphophinyl)hydroxylamine (1.35 g, 5.77 mmol) in THF (40 mL), cooled in a dry ice/acetone bath. The resulting mixture was stirred for 10 min at the same temperature then 18 h at room temperature. CH2Cl2 (40 mL) was added, the solids were removed by filtration and washed with several portions of CH2Cl2. The combined filtrates were concentrated in vacuo and purified by flash chromatography on silica gel using a gradient of 0-5% MeOH/EtOAc to provide aminobisphosphonate 24 as a clear yellow oil (1.24 g, 3.53 mmol, 59%). 1H NMR (400 MHz, CDCl3) δ 1.69 (bs, 2H), 3.52 (t, J=20.8 Hz, 1H), 4.64-4.67 (m, 8H), 5.24-5.27 (m, 4H), 5.36-5.42 (m, 4H), 5.92-6.02 (m, 4H).

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