Sodium Hydroxide → (2R,4R)-(+)-2-(hydroxymethyl)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidine

Participants

Reaction Steps

To an ice-cooled suspension of 690 mg of LiAlH4 (18.1 mmol) in 15 ml of dry ether was added 6.10 g (18.1 mmol) of (2R, 4R)-(+)-2-(ethoxycarbonyl)-4-(methoxymethoxy)-1-(4-methoxyphenethyl) pyrrolidine in 15 ml of dry ether and the mixture was stirred on ice for 30 min and at room temperature for 30 min. To the ice-cooled mixture 0.7 ml of water and 1N NaOH were added and the mixture was stirred for 30 min on ice, and for 30 min at room temperature. Magnesium sulfate was added and after stirring for 30 min, insoluble materials were filtered off on celite. The filtrate was concentrated in vacuo to give 5.30 g of (2R,4R)-(+)-2-(hydroxymethyl)-4-(methoxymethoxy)-1-(4-methoxyphenethyl)pyrrolidine (99.3%) as pale yellow oil.

Provenance & Evidence