Reaction #155405

Reaction equation

N-Boc-3-azetidinone

2-tert-butoxy-2-oxoethyl-zinc chloride

Et2O

→

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

Solvents

THF

Conditions

Workup

1. 1
   OtherThe reaction was then quenched with sat. aq. NH4Cl (10 mL)
2. 2
   Otherthe aqueous layer was separated
3. 3
   Extractionextracted with ethyl acetate (2×30 mL)
4. 4
   WashThe combined organic layers were washed with 5% aq. NaHCO3 (2×10 mL), brine (15 mL)
5. 5
   Dryingdried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated to dryness

Procedure

To a stirring solution of N-Boc-3-azetidinone (0.45 g, 2.64 mmol) in THF (5 mL) was slowly added a 0.5 M solution of 2-tert-butoxy-2-oxoethyl-zinc chloride in Et2O (10 mL, 5.0 mmol), and the reaction mixture was stirred for 5 h. The reaction was then quenched with sat. aq. NH4Cl (10 mL), and the aqueous layer was separated and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with 5% aq. NaHCO3 (2×10 mL), brine (15 mL), dried over Na2SO4, filtered and concentrated to dryness to yield tert-butyl-2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetate (MS m/e [M+H]+ calcd 288.2. found 287.7).

Source