Sodium hydride → HCID 58348398, compound

Participants

Reaction Steps

A solution of (S)-(+)-3-quinuclidinol (299 mg) and 1-phenyl-cycloheptanecarboxylic acid methyl ester (Example 14d) (455 mg) in 6.5 mL dry toluene under nitrogen was treated with a 60% dispersion of sodium hydride (94 mg) and the mixture was heated to reflux for 24 h then cooled to room temperature and allowed to stand over the weekend. EtOAc and sat. NaHCO3 (aq) were added and the phases separated. The aqueous phase was extracted with EtOAc (×3) and the combined organic layer was washed with brine, dried (MgSO4) and evaporated to afford the crude product. Purification was achieved by silica gel chromatography eluting with 0-10% MeOH/dichloromethane to give the sub-titled compound (384 mg) as a yellow oil.

Provenance & Evidence