Methyl N-(triethylammoniosulfonyl)carbamate → HCID 68691509, compound

Participants

Reaction Steps

To a solution of (R)-tert-butyl 3-((S)-4-acetamido-1-(6-fluoro-3′-methylbiphenyl-3-yl)-1-hydroxybutyl)piperidine-1-carboxylate (380 mg, 0.76 mmol) in anhydrous toluene (8 mL) was added Burgess reagent (352 mg, 1.47 mmol). The reaction mixture was stirred under reflux overnight. The solvent was removed and the residue was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residual oil was purified by preparative tlc to afford (S)-tert-butyl 3-(4-acetamido-1-(6-fluoro-3′-methylbiphenyl-3-yl)but-1-enyl)piperidine-1-carboxylate (110 mg, 30% yield). 1H NMR (400 MHz, MeOH):7.33-7.39 (m, 2 H), 7.13-7.23 (m, 2 H), 6.95-7.03 (m, 3 H), 5.29-5.33 (m, 1 H), 3.93-4.15 (m, 1 H), 3.78-3.91 (m, 1 H), 3.00-3.04 (m, 2H), 2.40-2.53 (m, 1 H), 2.37 (d, 3 H), 1.89 (s, 3 H), 1.75 (m, 1H), 1.44-1.62 (m, 4 H), 1.41 (s, 9 H), 1.16-1.32 (m, 3H), 1.01 (m, 1 H). MS (E/Z): 481 (M+H+)

Provenance & Evidence