Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (2S)-2-[(5-bromopyridin-2-yl)(phenyl)methoxy]-N-(cyanomethyl)-4-methylpentanamide

Participants

Reaction Steps

To a solution of (5-bromopyridin-2-yl)(phenyl)methyl 2,2,2-trichloroethanimidoate from example 53 step 2 (2 g, 4.9 mmol) in 1,2-dichloroethane (50 mL) was added (2S)-N-(cyanomethyl)-2-hydroxy-4-methylpentanamide (830 mg, 4.9 mmol, 1 eg) and camphor sulfonic acid (114 mg, 0.49 mmol, 0.10 eg). The suspension was heated to reflux for 18 hours, then concentrated to dryness. Residue was chromatographed with 25% EtOAc/hexane to yield the title compound.

Provenance & Evidence