Ammonium Chloride → HCID 66818552, compound

Participants

Reaction Steps

n-Butyllithium (1.6 M solution in hexane, 345 μl, 0.552 mmol) was added to a solution of {4-[4-chloro-2-(1,4-dioxa-8-aza-spiro[4.5]decane-8-sulfonyl)-butyl]-3,5-dimethyl-phenyl}-methyl-carbamic acid tert-butyl ester (115.0 mg, 0.2165 mmol) in THF (3.0 ml) at −78° C. over three minutes. The mixture was stirred at the same temperature for five minutes, and then warmed and further stirred at room temperature for one hour. A 50% saturated aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give {4-[1-(1,4-dioxa-8-aza-spiro[4.5]decane-8-sulfonyl)-cyclopropylmethyl]-3,5-dimethyl-phenyl}-methyl-carbamic acid tert-butyl ester and {4-[1-(1,4-dioxa-8-aza-spiro[4.5]decane-8-sulfonyl)-cyclopropylmethyl]-3,5-dimethyl-phenyl}-methyl-amine as a mixture (46.0 mg, 43% and 19.6 mg, 23%). This was used in the next reaction without complete purification.

Provenance & Evidence