Cyclopentanol → HCID 22032982, compound

Participants

Reaction Conditions

Reaction Steps

A 5 mL conical glass microwave reaction vessel with stir bar, sealed with a septum and swept with nitrogen, was charged with a solution of 0.08 g (0.22 mmol) 1-(benzenesulfonyl-5-(3-chlorophenyl)-1H-indole in 1.2 mL anhydrous toluene. 32 μL (0.33 mmol) cyclopentanol was added with stirring, followed by 0.3 mL 1.0 M solution of KOt-Bu in THF. The septum was removed and the vial was sealed with a cap. The reaction vessel was heated to 150° C. for 350 seconds in a microwave reactor (Personal Chemistry Inc., Milford, Mass.) and allowed to cool to room temperature. An aliquot removed for LC analysis indicated that the reaction was complete. The crude reaction mixture was taken up in 10 mL of brine and extracted with EtOAc. The organic phase was filtered through an 8 mL aqueous/organic separation column (Alltech Associates, Inc., Deerfield, Ill.) and was concentrated. The residue was purified by RP-HPLC (see Note 1 below) to give 11.2 mg 5-(3-chlorophenyl)-1-cyclopentyl-1H-indole as an oil.

Provenance & Evidence