Dimethyl Sulfoxide → HCID 59831615, compound

Participants

Reaction Steps

A suspension of NaH (23.4 mg, 0.928 mmol) in DMSO (1.2 ml, 16.9 mmol) was stirred at RT for 20 min. To this mixture was added a solution of [3-(1H-indol-5-yl)-3-phenyl-propyl]-methyl-carbamic acid tert-butyl ester LXXV (307 mg, 0.843 mmol) in Et2O (9 ml). The reaction mixture was stirred at room temperature for 40 minutes, after which MsCl (78.2 μl, 1.01 mmol) was added. The reaction mixture was stirred at room temperature for 2.5 hours followed by reflux for 2 hours. The mixture was partitioned between a saturated solution of NaHCO3 and Et2O. The aqueous layer was extracted with Et2O, and the combined organic layers were dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording [3-(1-Methanesulfonyl-1H-indol-5-yl)-3-phenyl-propyl]-methyl-carbamic acid tert-butyl ester LXXVI (56 mg, 15% yield) in a first fraction, and [3-(1,3-Bis-methanesulfonyl-1H-indol-5-yl)-3-phenyl-propyl]-methyl-carbamic acid tert-butyl ester LXXVII (45 mg, 10% yield) in a second fraction.

Provenance & Evidence