Ethyl chloroformate → [1-(4-Benzyloxy-3-methoxy-phenyl)-2-phenyl-ethyl]-(2,2-dimethoxy-ethyl)-carbamic acid ethyl ester

To a stirred solution of [1-(4-benzyloxy-3-methoxy-phenyl)-2-(3-methoxy-phenyl)-ethyl]-(2,2-dimethoxy-ethyl)-amine (10.46 g, 20 mmol) in tetrahydrofuran (40 mL) and water (20 mL) was added potassium carbonate (5 g, 36 mmol) and ethyl chloroformate (1.91 mL, 20 mmol) dropwise. The mixture was stirred for 1 h at room temperature. The mixture was diluted with diethyl ether (100 mL), and the organic layer was separated. The aqueous phase was extracted with ethyl acetate (3×100 mL) and the combined extracts were washed with saturated aqueous sodium chloride solution (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 20% ethyl acetate/hexane) afforded [1-(4-benzyloxy-3-methoxy-phenyl)-2-phenyl-ethyl]-(2,2-dimethoxy-ethyl)-carbamic acid ethyl ester (7 g, 67% yield in three steps) as a colorless oil.

1. customthe organic layer was separated
2. extractionThe aqueous phase was extracted with ethyl acetate (3×100 mL)
3. washthe combined extracts were washed with saturated aqueous sodium chloride solution (100 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORDレコード

ord-c4b7e633555a4bac8695ae2693a52845

出典データセット

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07067529B2