Sodium triacetoxyborohydride → HCID 20672399, compound

Participants

Reaction Steps

A solution of 2-(R)-(3-(R)formyl-4-(S)-phenylpyrrolidin-1-yl)-2-(cyclohexyl)acetic acid, (4-methoxy)benzyl ester (33 mg, 0.075 mmol, from EXAMPLE 33, Step E), 3-(tetrazolo[4,5-a]pyridin-5-yl)propylpiperidine.HCl (27 mg, 0.097 mmol from EXAMPLE 34, Step B) sodium triacetoxyborohydride, 32 mg (0.15 mmol) and TEA (0.014 mL, 0.097 mmol), in 1.0 mL 1,2-dichloroethane was stirred overnight. The solvent was removed and the product was purified by preprative HPLC (column: YMC Combiprep ODS-A 20×50 mm, gradient: 5% acetonitrile/H2O w/ 0.1% TFA for 1 min then ramp to 100% acetonitrile/H2O w/ 0.1% TFA over 6 min, flow: 20 mL/min). The material was stirred in 3 mL formic acid for 8 h. After removal of solvent the purification was accomplished by preprative HPLC (column: YMC Combiprep ODS-A 20×50 mm, gradient: 5% acetonitrile/H2O w/ 0.1% TFA for 1 min then ramp to 100% acetonitrile/H2O w/0.1% TFA over 6 min, flow: 20 mL/min) to give 11 mg (27%) of the title compound: 1H NMR (500 MHz) δ 1.02-1.98 (22H), 2.05-2.1 (m, 1H), 2.1-2.2 (m, 1H), 2.3-2.4 (m, 1H), 2.6-3.4 (8H), 3.8-3.9 (t, 2H), 4.51-4.55 (m, 1H), 7.2-7.33 (m, 5H), 7.48-7.49 (d, 1H, J=9 Hz), 7.94-7.96 (d, 1H, J=9 Hz): ESI-MS, M/z; (M+H)=545.5 (obs), 545.3 (calc.).

Provenance & Evidence