Trans-tert-butyl 3-(2-(benzyloxy)ethyl)-4-(2-hydroxy-4-methoxyphenyl)pyrrolidine-1-carboxylate → HCID 131731907, compound

Participants

Reaction Steps

To a solution of the product from Example 280C (450 mg, 1.05 mmol) in 20 mL of tetrahydrofuran was added wet 20% Pd(OH)2 in a 250 mL stainless steel pressure bottle. The vessel was capped and stirred for three hours under hydrogen (30 psi) at room temperature. The reaction was filtered through a nylon membrane and concentrated. The crude product was chromatographed on a silica gel column eluting with 3:1 ethyl acetate/hexane to afford the titled compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.24-1.59 (m, 11H) 2.35 (d, J=7.12 Hz, 1H) 2.86-2.98 (m, 1H) 3.06-3.18 (m, 2H) 3.48-3.71 (m, 5H) 3.96-4.06 (m, 2H) 4.36 (s, 1H) 6.32-6.41 (m, 2H) 7.03 (d, J=8.48 Hz, 1H) 9.42 (s, 1H).

Provenance & Evidence