反应 #73478
ord-7777638f717d4ab2ba422c9cc75a3e75
反应方程式
反应物
试剂
反应条件
后处理
- 1温度before being cooled to 0° C
- 2萃取The mixture was extracted twice with 50 mL of ethyl acetate
- 3洗涤washed with water and saturated sodium chloride solution
- 4干燥dried over magnesium sulfate
- 5浓缩concentrated in vacuo
- 6workup.DISSOLUTIONThe crude alcohol was dissolved in 5 mL of tetrahydrofuran
- 7workup.ADDITIONwere added
- 8workup.STIRRINGThe reaction mixture was stirred for 1 h at room temperature
- 9其他The reaction mixture was evaporated to dryness
实验过程
16.5 mL (8.23 mmol) of a 0.5M solution of 9-BBN in tetrahydrofuran were added to a solution of 1.09 g (2.74 mmol) of 2-methyl-propane-2-sulfinic acid {1-[8-(4-fluoro-phenyl)-1,4-dioxa-spiro[4.5]dec-8-yl]allyl}-amide (106) in 5 mL THF at 0° C. The reaction mixture was allowed to warm to room temperature over night, before being cooled to 0° C. Then, 20 mL of 3M aqueous sodium hydroxide and 7.5 mL of 30% aqueous hydrogen peroxide were added slowly, and the mixture was stirred for 16 h at room temperature. The mixture was extracted twice with 50 mL of ethyl acetate, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. The crude alcohol was dissolved in 5 mL of tetrahydrofuran and added slowly to a suspension of 131 mg (4.46 mmol) of sodium hydride (60%) in 5 mL tetrahydrofuran at 0° C. 515 μL (8.20 mmol) of iodomethane were added, and after stirring for 16 h at room temperature another 50 mg of sodium hydride (60%) were added. The reaction mixture was stirred for 1 h at room temperature, then 30 mL of methanol and 15 mL of aqueous ammonium hydroxide solution (33%) were added. The reaction mixture was evaporated to dryness and lyophilized from water to give 1.17 g of the title compound (107) in a purity sufficient for further conversion. Rt=0.93 min (Method 18). Detected mass: 428.2 (M+H+).