反应 #1178474

ord-644f17aedce74d7fad738d794b62b014

反应方程式

O=C1CN(C(c2ccccc2)c2ccccc2)C1
1-benzhydrylazetidin-3-one
C[CH2][Mg][Br]
ethylmagnesium bromide
O=C([O-])O.[Na+]
sodium hydrogen carbonate
CCC1(O)CN(C(c2ccccc2)c2ccccc2)C1
title compound
收率 60.0%
CCC1(O)CN(C(c2ccccc2)c2ccccc2)C1
1-Benzhydryl-3-ethylazetidin-3-ol
收率 60.0%

反应条件

温度
-10°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    过滤Then, the reaction liquor was filtered through celite
  2. 2
    萃取the filtrate was extracted with ethyl acetate
  3. 3
    洗涤The extract was washed with saturated brine
  4. 4
    干燥dried over anhydrous sodium sulfate
  5. 5
    其他Sodium sulfate was separated by filtration
  6. 6
    浓缩the solvent was concentrated under reduced pressure
  7. 7
    其他The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40M, ethyl acetate/n-hexane=1/9 to 6/4)

实验过程

To a tetrahydrofuran solution (10 mL) of 1-benzhydrylazetidin-3-one (3.23 g, 13.61 mmol), a 1M-tetrahydrofuran solution of ethylmagnesium bromide (13.61 mL, 27.22 mmol) was added at −78° C. under a nitrogen stream, and the mixture was allowed to warm to −10° C. over 5 hours. A saturated aqueous solution of sodium hydrogen carbonate (20 mL) was added to the reaction liquor, and the mixture was stirred for 15 minutes. Then, the reaction liquor was filtered through celite, and the filtrate was extracted with ethyl acetate. The extract was washed with saturated brine, and then dried over anhydrous sodium sulfate. Sodium sulfate was separated by filtration, and the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40M, ethyl acetate/n-hexane=1/9 to 6/4), to obtain the title compound (2.18 g, 60%) as an oily matter.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08129366B2uspto-grants-2012_03