Diethyl Ether → HCID 68914714, compound

Participants

Reaction Steps

[(S)-6-(4-Acetyl-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propyl-carbamic acid tert-butyl ester (400 mg, 0.71 mmol) was dissolved in tetrahydrofuran (15 ml) at 0° C. A 3 molar solution of methylmagnesium bromide in diethyl ether (2.82 ml, 7.12 mmol) was added slowly and the reaction mixture was stirred for 3 hours at room temperature. Another portion of a 3 molar solution of methylmagnesium bromide in diethyl ether (0.5 ml, 1.26 mmol) was added. Since no further conversion was observed, the reaction mixture was evaporated to dryness. Water (20 ml) was added to the residue and the aqueous phase was extracted with diethyl ether (50 ml) twice. The organic layer was dried over magnesium sulfate, filtered, and evaporated to dryness to yield the crude product. The crude product was purified by MPLC chromatography using dichloromethane/methanol (100:0-70:30) as eluent, yielding the product (300 mg, 47% purity, 39%).

Provenance & Evidence