Methanol → N-[(3R)-1-Azabicyclo[2.2.2]Oct-3-yl]4-Phenoxybenzamide

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Reaction Steps

TEA (50 μL, 0.35 mmol) is added to a suspension of 4-phenoxybenzoic acid (75 mg, 0.35 mmol) in CH2Cl2 (1 mL). Diphenylchlorophosphate (62, μL, 0.3 mmol) is added and the resulting solution is stirred at room temperature for 30 minutes. A solution of (R)-3-aminoquinuclidine (IM in DMF, 0.2 mL, 0.2 mmol) is added and the resulting solution is stirred overnight at room temperature. MeOH is added and the mixture is poured through a column of AG50 W ×2 ion exchange resin (H+form). The resin is washed with MeOH and then the product is eluted with 5% TEA in MeOH. The eluent is evaporated to dryness to yield the desired product (49 mg, 76%). MS for C2GH22N2O2 (ESI) (M+H)+ m/z 323.

Provenance & Evidence