反应 #1178470

ord-87cecb4c941d4d2a8bcb8345b41b0ae2

反应方程式

C1CCOC1
tetrahydrofuran
[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminum hydride
C1CCOC1
tetrahydrofuran
COC(=O)C1CN(C(c2ccccc2)c2ccccc2)C1
1-benzhydrylazetidin-3-carboxylic acid methyl ester
[Na+].[OH-]
sodium hydroxide
OCC1CN(C(c2ccccc2)c2ccccc2)C1
title compound
收率 108.6%
OCC1CN(C(c2ccccc2)c2ccccc2)C1
(1-Benzhydrylazetidin-3-yl)methanol
收率 108.6%

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    workup.STIRRINGthe reaction mixture was stirred for 3.5 hours
  2. 2
    workup.STIRRINGWhile the reaction mixture was stirred again under ice cooling
  3. 3
    workup.STIRRINGthe mixture was stirred for 20 minutes
  4. 4
    其他Precipitated insoluble matter was removed through separation by filtration
  5. 5
    浓缩the obtained mother liquor was concentrated under reduced pressure

实验过程

To an anhydrous tetrahydrofuran solution (100 mL) of lithium aluminum hydride (1.14 g, 29.93 mmol), a tetrahydrofuran solution (50 mL) of 1-benzhydrylazetidin-3-carboxylic acid methyl ester (Oakwood Products, Inc.: Code No. W07L) (2.00 g, 7.16 mmol) was added dropwise over 10 minutes under ice cooling and stirring, and the reaction mixture was stirred for 3.5 hours. While the reaction mixture was stirred again under ice cooling, water (1.14 mL), a 4N-aqueous solution of sodium hydroxide (1.14 mL) and water (4.50 mL) were added to the reaction liquor, and the mixture was stirred for 20 minutes. Precipitated insoluble matter was removed through separation by filtration, and the obtained mother liquor was concentrated under reduced pressure to obtain the title compound (1.97 g, over yield) as an oily matter.

来源

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