Formaldehyde → HCID 70162828, compound

Participants

Reaction Steps

To a rapidly stirred solution of (S)-3-{[5-(2-adamantan-1-yl-ethyl)-2-pyrrolidin-2-yl-1H-imidazole-4-carbonyl]-amino}-benzoic acid benzyl ester (Example 136, step d) (180 mg, 0.33 mmol) and formaldehyde (100 μl, 37% aqueous) in dichloroethane (5 ml) was added sodium triacetoxyborohydride (100 mg, 0.47 mmol). After stirring for 1 h at room temperature the reaction mixture was diluted with DCM and the solution was washed with saturated sodium bicarbonate. The organic layer was dried (MgSO4) and the solvent was evaporated. The residue was purified by flash column chromatography (silica, DCM/hexane/IPA, 9:9:2) to afford the product as a white solid (130 mg, 71%). 1H NMR (300 MHz, CDCl3) 9.70 (1H, br s), 9.12 (1H, s), 8.17 (1H, d), 8.12 (1H, s), 7.77 (1H, d), 7.47-7.35 (6H, m), 5.37 (2H, s), 3.41 (1H, m), 3.20 (1H, m), 3.06 (2H, m), 2.30 (4H, s+m),1.96-1.55 (19H, m), 1.42 (2H, m).

Provenance & Evidence