Reaction #7548

Reaction equation

1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol

isopropanol

nitric acid

→

1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol nitrate

Solvents

ethyl acetate

ethyl acetate

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Otherat room temperature
3. 3
   workup.WAITat 5° C. for 1 hour
4. 4
   OtherThe crystals precipitated
5. 5
   Filtrationwere collected by filtration

Procedure

In 20 mL of ethyl acetate was dissolved 10.0 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol, and 20 mL of isopropanol was added thereto, after which 2.60 mL of concentrated nitric acid (61%) was added dropwise thereto at room temperature. To the reaction mixture was added dropwise 60 mL of ethyl acetate, and the resulting mixture was stirred at the same temperature for 1 hour and then at 5° C. for 1 hour. The crystals precipitated were collected by filtration to obtain 11.3 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol nitrate as colorless crystals.

Source