Tetrabutylammonium Fluoride → HCID 10870530, compound

A solution of 2.01 g (7.68 mmol) of tetrabutylammonium fluoride in 5 ml of tetrahydrofuran was added, whilst ice-cooling, to a solution of 2.16 g (5.12 mmol) of (2S,3S)-1-t-butoxycarbonyl-2-benzyloxymethyl-3-t-butyldimethylsilyloxypyrrolidine in 5 ml of tetrahydrofuran, and the mixture was stirred at room temperature for 4 hours. At the end of this time, the reaction mixture was diluted with ethyl acetate, and the organic extract was washed with 0.5N aqueous hydrochloric acid, with a 5% w/v aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The reaction mixture was then dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The resulting residue was then purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.57 g of the title compound as an oil.

1. extractionthe organic extract
2. washwas washed with 0.5N aqueous hydrochloric acid, with a 5% w/v aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
3. dry with materialThe reaction mixture was then dried over anhydrous sodium sulfate
4. customafter which the solvent was removed by distillation under reduced pressure
5. customThe resulting residue was then purified by column chromatography through silica gel
6. additionby volume mixture of hexane and ethyl acetate as the eluent

ORD record

ord-7329979b60874b7eba7261522e180d93

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05629406