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

Participants

Reaction Steps

To a solution of trans-3-(3-Cyclopentoxy-4-methoxyphenyl)-4-methoxycarbonyl-1-(phenylmethyl)pyrrolidine (2.7 g, 6.6 mmol) in 27 mL of THF at 0° C. was added LiAlH4 (4.0 mmol, 4 mL of 1M toluene solution). After stirring for 2 hr the reaction mixture was then successively treated dropwise with H2O (0.15 mL), 15% NaOH (0.15 mL), and H2O (0.46 mL). The resulting suspension was diluted with ether, stirred for 1 hr, filtered through Celite, and concentrated under reduced pressure to an oil. Silica gel chromatography (graded elution: CH2Cl2 then 9:1, CH2Cl2 :methanol) provided trans-3-(3-cyclopentoxy-4-methoxyphenyl)-4-hydroxymethyl-1-(phenylmethyl)pyrrolidine (2.0 g, 80%) as an oil.

Provenance & Evidence