Acetonitrile → HCID 69883189, compound

Participants

Reaction Steps

To 117 mg (0.32 mmol) (S)-toluene-4-sulfonic acid 8-ethoxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester was added 84 mg (0.33 mmol) 3-naphthalen-2-yl-8-aza-bicyclo[3.2.1]octan-3-ol, 95.0 mg K2CO3, and 7 mL acetonitrile. The reaction was refluxed and was monitored by TLC on a silica gel plate using CHCl3:MeOH (10:1) as eluent. After 18 h, the mixture was transferred to a separatory funnel containing 50 mL water. The aqueous layer was extracted with CH2Cl2 (2×25 mL), washed with brine, dried over Na2SO4, filtered and evaporated to an oil. The crude material was purified by flash chromatography on silica gel, using a gradient elution of CHCl3:MeOH (40:1 to 20:1). The appropriate fractions were combined and evaporated to afford 68.1 mg (0.15 mmol, a 48% yield) of the title compound as a tan solid.

Provenance & Evidence