Reaction #155406

Reaction equation

BOC2O

NaOH

tert-butyl-2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetate

HCl

→

2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetic acid

Yield 94.0%

Solvents

dioxane

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was then cooled to 0° C.
2. 2
   Temperatureto warm to room temperature for 2 h
3. 3
   Concentrationwas then concentrated to half its total volume on the rotary evaporator
4. 4
   workup.ADDITIONIsopropanol (3 mL) and chloroform (12 mL) were then added
5. 5
   Temperaturethe mixture was cooled to 0° C.
6. 6
   OtherThe organic layer was then separated
7. 7
   Dryingdried over Na2SO4
8. 8
   Concentrationconcentrated to dryness

Procedure

To a stirring solution of tert-butyl-2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetate (0.86 g, 2.99 mmol) in dioxane (18 mL) was added 3M HCl (5 mL), and the mixture was heated at 70° C. for 1 h. The reaction mixture was then cooled to 0° C. and it was basified with 2 M NaOH (8 mL), followed by addition of BOC2O (1.0 g, 4.6 mmol). The reaction mixture was allowed to warm to room temperature for 2 h, and was then concentrated to half its total volume on the rotary evaporator. Isopropanol (3 mL) and chloroform (12 mL) were then added and the mixture was cooled to 0° C. and slowly acidified to pH 3 with 1M HCl. The organic layer was then separated, dried over Na2SO4, and concentrated to dryness to yield 2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetic acid (0.65 g, 2.81 mmol, 94.0% yield).

Source