反应 #1909786

ord-6b18786248a543a8af2f48fefd0f861d

反应方程式

N[C@H](CO)Cc1ccccc1
L-phenylalaninol
[H-].[Na+]
sodium hydride
BrCc1ccccc1
benzyl bromide
N[C@H](COCc1ccccc1)Cc1ccccc1
title compound
收率 77.0%
N[C@H](COCc1ccccc1)Cc1ccccc1
O-Benzyl-L-phenylalaninol
收率 77.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他at room temperature
  2. 2
    温度Twenty minutes later, the reaction mixture was refluxed
  3. 3
    温度under heating for 1 hour
  4. 4
    温度to cool
  5. 5
    温度cooling
  6. 6
    萃取extracted with ether
  7. 7
    萃取The organic layer was extracted with 10% hydrochloric acid
  8. 8
    萃取extracted with ether
  9. 9
    洗涤The organic layer was washed with saturated brine
  10. 10
    干燥dried over anhydrous magnesium sulfate
  11. 11
    浓缩concentrated under reduced pressure

实验过程

To a solution of L-phenylalaninol (11.78 g) in THF (200 ml) was gradually added 60% sodium hydride (3.43 g) in oil at room temperature. Twenty minutes later, the reaction mixture was refluxed under heating for 1 hour. Then, the mixture was allowed to cool, followed by gradual addition of benzyl bromide (9.27 ml) under ice-cooling, and stirred at room temperature for 16 hours. The reaction mixture was added to saturated brine, and extracted with ether. The organic layer was extracted with 10% hydrochloric acid. The aqueous layer was made alkaline with an aqueous sodium hydroxide solution, and extracted with ether. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (14.5 g, yield 77%).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: USRE039088E1uspto-grants-2006_05