Hydrochloric Acid → (2R,4R)-[4-(4-Bromo-2-nitro-phenylamino)-pyrrolidin-2-yl]-methanol, hydrochloride

Participants

Reaction Steps

To a solution of (2R,4R)-4-(4-bromo-2-nitro-phenylamino)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (125.5 g, 0.301 mol) in dichloromethane (400 mL) add 4 N hydrochloric acid in dioxane (800 mL) and stir for 4 h at room temperature. Collect the precipitate by filtration, wash with ether and dry at 20 mm Hg/60° C. to obtain the title compound (105.2 g, 99%). [α]D20−89.6 (c=1.0 in methanol). 1H NMR (400 MHz, DMSO-d6) δ 1.80-1.85 (m, 1H), 2.54-2.59 (m, 1H), 3.43-3.51 (m, 3H), 3.56-3.63 (m, 1H), 3.69-3.72 (m, 2 H), 4.50-4.51 (m, 1H), 5.60 (br s, 1H), 7.10 (d, 1H), 7.65 (dd, 1H), 8.14 (d, 1H), 8.95 (br s, 1H), 9.91 (br s, 1H).

Provenance & Evidence