Formaldehyde → HCID 10401484, compound

Participants

Reaction Steps

To a solution of 6-(4-amino-phenylsulfanyl)-hexanoic acid methyl ester (2.5 g, 10 mmol) in methanol (20 mL) was added at 0° C. a 37% aqueous solution of formaldehyde (2.4 mL, 30 mmol) and a solution of sodium cyanoborohydride (2.5 g, 40 mmol) and zinc chloride (2.7 g, 20 mmol) in methanol (150 mL). The mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The residue was taken up in ethyl acetate (250 mL) and aqueous sodium hydroxide (100 mL, 2M). The organic layer was washed consecutively with aqueous sodium hydroxide (100 mL, 2M), distilled water (2×100 mL) and brine (2×100 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a yellow oil that was purified by flash chromatography (10:90:1 to 20:80:1 ethyl acetate:40-60° C. petroleum ether:triethylamine) to give the title compound (2.2 g, 79%) as a colourless oil.

Provenance & Evidence