Methanol → HCID 49847999, compound

Participants

Reaction Steps

Charge a 1 L flask with ammonium formate salt (39.0 g, 618.0 mmoles) and 10% Pd/C (3.91 g) and (S)-benzyl 5-((3,5-bis(trifluoromethyl)benzyl)(2-methyl-2H-tetrazol-5-yl)amino)-7,9-dimethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylate (39.1 g, 61.8 mmoles) dissolved in MeOH (391 mL, 966 moles). Stir the resulting slurry at RT and monitor by HPLC. After the reaction is complete, filter to collect the solid. Rinse the solid with MeOH (100 mL). Combine the filtrate solutions and organic washes and then dry over Na2SO4. Filter and concentrate to dryness. Dissolve in MeOH (92 mL) and seed with seed crystals of the titled compound. Cool and store over night to yield 14.03 g, 45.5% of the titled compound, 99.92% ee by HPLC.

Provenance & Evidence