(2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-(4-biphenyloxy)methyl-n-tert-butoxycarbonylpyrrolidine → (2S,4R)-4-Glycylamino-2-(4-Biphenyloxy)methylpyrrolidine

Participants

Reaction Steps

(2S,4R)-4-(N-tert-Butoxycarbonylglycylamino)-2-(4-biphenyloxy)methyl-N-tert-butoxycarbonylpyrrolidine (B, 431 mg) was dissolved in 4 N hydrogen chloride in 1,4-dioxane (4 mL). After stirring for 2 hr, the reaction mixture was evaporated in vacuo to give a white solid. The solid was washed with ether to afford the titled compound (254 mg): 1H NMR (400 MHz, D2O) δ 2.33 (m, 1H), 2.44 (m, 1H), 3.45 (dd, J=12.7, 4.4 Hz, 1H), 3.79 (dd, J=12.7, 6.8 Hz, 1H), 3.84 (s, 2H), 4.27 (dd, J=10.7, 6.8 Hz, 1H), 4.36 (m, 1H), 4.47 (d, J=10.7 Hz, 1H), 4.67 (m, 1H), 7.16 (d, J=8.3 Hz, 2H), 7.43 (d, J=7.3 Hz, 1H), 7.53 (t, J=7.3 Hz, 2H), 7.68-7.72 (m, 4H).

Provenance & Evidence