3-(2-Chloro-5-nitro-phenoxymethyl)-azetidine-1-carboxylic acid tert-butyl ester → 3-(5-Amino-2-chloro-phenoxymethyl)-azetidine-1-carboxylic Acid Tert-Butyl Ester

Temperature

0 °C

To a solution of 3-(2-chloro-5-nitro-phenoxymethyl)-azetidine-1-carboxylic acid tert-butyl ester (2.5 g, 7.29 mmol) in 60 mL of MeOH/H2O (1:1) and 3 mL of acetic acid (J. T. Baker) was added Zn powder (2.3 g, 36.47 mmol, Aldrich) at 0° C. The reaction mixture was stirred at 0° C. for 2 h then stirred at 10° C. for 2 h. The resulting mixture was filtered through a Celite® pad and the filtrate was concentrated in vacuo. The residue was treated with 60 mL of saturated aqueous NaHCO3 and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine and dried with MgSO4. The resulting solution was concentrated in vacuo and the title compound was obtained by column chromatography (silica gel, EtOAc) as a yellow solid.

1. stirringthen stirred at 10° C. for 2 h
2. filtrationThe resulting mixture was filtered through a Celite® pad
3. concentrationthe filtrate was concentrated in vacuo
4. additionThe residue was treated with 60 mL of saturated aqueous NaHCO3
5. extractionextracted with EtOAc (3×50 mL)
6. washThe combined organic layers were washed with brine
7. dry with materialdried with MgSO4
8. concentrationThe resulting solution was concentrated in vacuo

ORD record

ord-ef12ecd2298b4f5792294bea1853b34b

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247430B2