Ammonium Chloride → HCID 22927097, compound

Participants

Reaction Conditions

Reaction Steps

9.5 g of Ethyl 2-isopropoxyacetate was dissolved in 200 ml of tetrahydrofuran anhydride, and the mixture was cooled to −78° C. under nitrogen atmosphere. After adding 6.5 ml of lithium bis(trimethylsilyl)amide (1M solution in tetrahydrofuran), 15 g of 3-benzyloxybenzaldehyde in tetrahydrofuran (50 ml) was added via a cannula. The temperature of the solution was elevated to room temperature, and the mixture was stirred for 3 hours. The reaction solution was treated with saturated aqueous ammonium chloride, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was distilled off. The residue was purified by silica gel column chromatography, to give 10.8 g of ethyl 3-[3-(benzyloxy)phenyl]-3-hydroxy-2-isopropoxypropanoate as a mixture of erythro and threo in the 3:1 hexane-ethyl acetate fraction. This product was dissolved in 50 ml of pyridine and 3.5 ml of methanesulfonyl chloride was added under ice-cooling. After stirring overnight at room temperature, the reaction mixture was diluted with ethyl acetate, and washed with 1N hydrochloric acid. The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was distilled off, to give 13.7 g of ethyl 3-[3-(benzyloxy)phenyl]-2-isopropoxy-3-[(methylsulfonyl) oxy]propanoate. This product was dissolved in 450 ml of ethanol, 3.9 g of 10% palladium carbon was added, and the mixture was stirred overnight at room temperature under hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was concentrated, to give 7.5 g of the title compound.

Provenance & Evidence