trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine

Participants

Reaction Steps

trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine (3.5 g, 8.6 mmol) was dissolved in 20 mL of 4% HCO2H:methanol. While stirring at room temperature, 10% Pd/C (450 mg) was added in small portions. After several hours the reaction was diluted with methanol. Filtration through Celite followed by concentration under reduced pressure yielded a yellow oil residue. This residue was partitioned between CH2Cl2 and sat. NaHCO3. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2×). The organic layers were combined, dried (K2CO3), filtered, and concentrated under reduced pressure to afford a pale oil. Chromatography on silica gel (8:1:1, CH2Cl2 :ethyl acetate:methanol) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine as a colorless oil (2.3 g, 84%). 1H-NMR (300 MHz): δ 2.86-3.04 (m, 2), 3.29-3.52 (m, 4), 3.68 (s, 3), 3.83 (s, 3).

Provenance & Evidence