Diisopropylethylamine → 2-(4-Methoxy-5-nitrophenyl)-N-methyl-N-[(1S)-1-phenyl-2-(1-pyrrolidinyl)ethyl]-acetamide

Participants

Reaction Steps

To a solution of acid (iii)(17.5 g, 85.78 mmol) in anhydrous CH2Cl2 (175 mL) was added 1-hydroxybenzotriazole hydrate (11.58 g, 85.78 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 18.02 g, 94.36 mmol). After stirring the reaction mixture at room temperature for 30 min, a solution of the diamine (iv-a)(16.00 g, 78.43 mmol) in anhydrous CH2Cl2 (60 mL) was added, followed by N,N-diisopropylethylamine (10.43 g, 80.0 mmol). The reaction mixture was stirred at room temperature for 72 h. The reaction mixture was quenched with saturated sodium bicarbonate solution and the organic layer was separated, washed with saturated salt solution and dried over anhydrous sodium sulfate. The removal of CH2Cl2 under reduced pressure gave crude compound (v-a) as dark brown oil. The product (v-a) was purified on a silica gel column to give a yellow syrup, 31 g (99%); 1HNMR (CDCl3, 300 MHz) δ1.74 (m, 4H), 2.75 (s, 3H), 3.95 (s, 3H), 6.10 (m, 1H), 7.05-7.75 (m, 8H).

Provenance & Evidence