Triethylamine → HCID 20664090, compound

Participants

Reaction Steps

A solution of 2-(R)-(3-(R)-Formyl-4-(S)-(3-fluorophenyl) pyrrolidin-1-yl)-4,4-dimethylpentanoic acid, benzyl ester (27 mg, 0.065 mmol, from Step B) in 2 mL methanol was stirred over 20 mg 10% Pd/C under 1 atm of hydrogen. After 1 h the mixture was filtered and concentrated. The crude material was dissolved in 2 mL DCE and 4-(4-Benzyl-1-ethyl-(1H-pyrazol-5-yl))-piperidine HCl (26 mg, 0.085 mmol, from EXAMPLE 8 Step F), triethylamine (21 μL, 0.15 mmol) and sodium triacetoxyborohydride (32 mg, 0.15 mmol) were added. The solution was stirred overnight then Boc anhydride (19 mg, 0.085 mmol) was added and stirring was continued for 3 h. The mixture was concentrated and the product was purified by flash chromatography (95/5 DCM/MeOH→95/5/0.5 DCM/MeOH/NH4OH) to afford 14 mg (37%) of the title compound. 1H NMR (500 MHz, CDCl3). δ1.03 (s, 9H), 1.31-1.34 (t, 3H), 1.36-1.45 (m, 1H), 1.5-1.59 (m, 1H), 1.64-1.72 (m, 2H), 1.76-1.8 (d, 1H), 1.91-2.0 (m, 2H), 2.08-2.13 (t, 1H), 2.37-2.4 (dd, 1H), 2.46-2.6 (m, 2H), 2.77-2.8 (m, 2HO, 2.96-3.0 (d, 1H), 3.18-3.37 (m, 2H), 3.56-3.6 (d, 1H), 3.7-3.82 (m, 2H), 3.85 (s, 2H), 4.01-4.05 (q, 2H), 5.72 (s, 1H), 6.97-7.0 (t, 1H), 7.13-7.2 (m, 5H), 7.22-7.28 (m, 2H), 7.33-7.4 (m, 1H). ESI-MS, M/z; (M+H)=575.6 (obs), 575.37 (calc.).

Provenance & Evidence