반응 #155406

반응 방정식

BOC2O

NaOH

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

HCl

→

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

수율 94.0%

용매

dioxane

반응 조건

후처리

1. 1
   온도The reaction mixture was then cooled to 0° C.
2. 2
   온도to warm to room temperature for 2 h
3. 3
   농축was 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
   온도the mixture was cooled to 0° C.
6. 6
   기타The organic layer was then separated
7. 7
   건조dried over Na2SO4
8. 8
   농축concentrated to dryness

실험 절차

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).

출처