Water → HCID 57718346, compound

A solution of tetra-n-butylammonium fluoride trihydrate(1.3 g, 4.2 mmol) in tetrahydrofuran (20 mL) was added to a solution of 2-(N-tert-butoxycarbonyl-N-methylamino)-4-(tert-butyldimethylsilyloxymethyl)pyridine (Reference compound No. 6-1, 1.4 g, 3.7 mmol) in tetrahydrofuran (20 mL) for 5 minutes at room temperature, and the mixture was stirred for 15 minutes. Ethyl acetate (50 mL) and water (100 mL) were added to the reaction mixture, the whole was separated, and then the aqueous layer was extracted with ethyl acetate (50 mL). These organic layers were combined, then it was washed with brine (100 mL) and dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure, then the resulting residue was purified by silica gel column chromatography to give 450 mg of the title reference compound as a reddish brown oil. (Yield 50%)

1. customthe whole was separated
2. extractionthe aqueous layer was extracted with ethyl acetate (50 mL)
3. washit was washed with brine (100 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. customThe organic layer was evaporated under reduced pressure
6. customthe resulting residue was purified by silica gel column chromatography
7. customto give 450 mg of the title reference compound as a reddish brown oil

ORD record

ord-002b3a3761e840a680ab483067a50553

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544703B2