Reaktion #66337

Reaktionsgleichung

N-Boc-3-azetidinone

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

Et2O

→

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was then quenched with sat. aq. NH4Cl (10 mL)
2. 2
   Sonstigethe aqueous layer was separated
3. 3
   Extraktionextracted with ethyl acetate (2×30 mL)
4. 4
   WaschenThe combined organic layers were washed with 5% aq. NaHCO3 (2×10 mL), brine (15 mL)
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated to dryness

Vorschrift

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).

Quelle