Formaldehyde → HCID 10408174, compound

To a solution of 6-(4-amino-phenylsulfanyl)-hexanoic acid methyl ester (1.5 g, 5.9 mmol) in methanol (60 mL) was added a solution of 4-chlorobenzaldehyde (834 mg, 5.9 mmol) in methanol (10 mL). After 1 hour of stirring at room temperature, the solution was cooled at 0° C. and a 37% aqueous solution of formaldehyde (1.44 g, 17.8 mmol) was added. A solution of sodium cyanoborohydride (1.49 g, 23.7 mmol) and zinc chloride (11.9 mmol) in methanol (60 mL) was added in a dropwise. The resulting mixture was stirred at room temperature for 1 hour and concentrated under reduced pressure. The residue was taken up in ethyl acetate (100 mL) and aqueous sodium hydroxide (75 mL, 2M). The organic layer was washed consecutively with aqueous sodium hydroxide (75 mL, 2M), distilled water (2×75 mL) and brine (75 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give an yellow oil that was purified by flash chromatography (5:95:1 to 20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine). The title compound was obtained as a colourless oil (2.2 g, 83%).

1. temperaturethe solution was cooled at 0° C.
2. stirringThe resulting mixture was stirred at room temperature for 1 hour
3. concentrationconcentrated under reduced pressure
4. washThe organic layer was washed consecutively with aqueous sodium hydroxide (75 mL, 2M)
5. distillationdistilled water (2×75 mL) and brine (75 mL)
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto give an yellow oil that
10. customwas purified by flash chromatography (5:95:1 to 20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine)

ORD record

ord-ef80bfb3e9d14a969dce58ecc98aee32

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683185B2