Water → trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-(hydroxymethyl)pyrrolidine

Participants

Reaction Conditions

Reaction Steps

To a solution of trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(methoxycarbonyl)pyrrolidine (500 mg, 1.57 mmol) in 7 mL of THF at 0° C. was added LiAlH4 (60 mg, 1.57 mmol). The resulting mixture was stirred for 15 min at 0° C. and then allowed to stir at room temperature for 20 min. The mixture was then successively treated dropwise with H2O (0.06 mL), 15% NaOH (0.06 mL), and H2O (0.18 mL). The resulting suspension was then stirred for 1 hr, filtered through Celite, and concentrated under reduced pressure to an oil. Silica gel chromatography (1:1 CHCl3 :methanol) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-(hydroxymethyl)pyrrolidine as a pale yellow oil (329 mg, 72%). 1H-NMR (300 MHz): δ 2.35 (m, 1), 2.90-3.08 (m, 3), 3.30-3.76 (m, 4), 3.82 (s, 3).

Provenance & Evidence