Nafoxidine Hydrochloride → rac 7-Methoxy Lasofoxifene

Participants

Reaction Steps

A solution of 1-{2-[4-(6-methoxy-2-phenyl-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine hydrochloride (nafoxidene hydrochloride) (1.0 g, 2.16 mmol) in 20 mL of absolute ethanol containing 1.0 g of palladium hydroxide on carbon was hydrogenated at 50 psi at 20° C. for 19 hr. Filtration and evaporation provided 863 mg (93%) of cis-1-{2-[4-(6-methoxy-2-phenyl-1,2,3,4-tetrahydronaphthalen-1-yl) phenoxy]ethyl}pyrrolidine: 1H-NMR (CDCl3): δ3.50-3.80 (m, 3 H), 3.85 (s, 3 H), 4.20-4.40 (m, 3 H), 6.80-7.00 (m, 3 H); MS 428 (P++1).

Provenance & Evidence