HRID1937720

反应详情

EQUATION

反应方程式

HRID 1937720 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

2

PROCEDURE

实验过程

Refering to FIG. 6, 4-Dimethylaminopyridine (DMAP) (0.31 g, 2.5 mmol) was added to a solution of methylphosphonic dichloride (0.332 g, 2.5 mmol, 31P NMR s, 43.93 ppm) stirring at room temperature under positive pressure argon gas. The resulting clear, colorless solution was cooled to −70° C. and a solution of cholesterol (0.97 g, 2.5 mmol) in anhydrous dichloromethane (20 ml) was added via syringe with vigorous stirring over a period of one hour. The reaction mixture was allowed to warm to room temperature and was maintained for 18 hours at which time 31P NMR analysis of a small aliquot of the reaction mixture indicated complete reaction (d, 39.08 ppm). Crude (13) was treated with additional DMAP (0.31 g, 2.5 mmol) and the reaction mixture cooled to −70° C. while stirring under positive pressure argon. Tris(2-aminoethyl)amine (TREN) (0.37 ml, 2.5 mmol) in anhydrous dichloromethane (20 ml) was added dropwise via syringe over a period of two hours. The reaction mixture was warmed to room temperature and stirred for an additional 18 hours (reaction complete by 31P NMR). Direct loading onto flash silica followed by a gradient of 10 to 20% MeOH/dichloromethane with 1 to 4% NH4OH gave 0.442 g of (18) as a white foam: (yield,28% over two steps), 31P NMR (d, 32.57 ppm), mass spec. calcd=592.89, found=593.49.

WORKUP

后处理

  1. temperatureThe resulting clear, colorless solution was cooled to −70° C.
  2. stirringwith vigorous stirring over a period of one hour
  3. temperatureto warm to room temperature
  4. temperaturewas maintained for 18 hours at which time 31P NMR analysis of a small aliquot of the reaction mixture
  5. customreaction (d, 39.08 ppm)
  6. temperaturethe reaction mixture cooled to −70° C.
  7. stirringwhile stirring under positive pressure argon
  8. temperatureThe reaction mixture was warmed to room temperature
  9. stirringstirred for an additional 18 hours
  10. custom(reaction complete by 31P NMR)