Acetic Acid → HCID 69332915, compound

Participants

Reaction Steps

To a stirred solution of methyl cis-4-[[1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]methylamino]cyclohexanecarboxylate (300 mg, 0.55 mmol), HCHO (300 ml), and AcOH (66 mg, 1.1 mmol) in MeOH (10.0 ml) was added NaBH3CN (70 mg, 1.1 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. After concentrated in vacuo, water was added and extracted with CH2Cl2. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo. The residue was purified by TLC with MeOH—CH2Cl2 (3:97, v/v) as eluent to give methyl 4-[N-[1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethyl]-N-methylamino]cyclohexanecarboxylate (160 mg, 52%) as an amorphous solid. 1H-NMR (CDCl3) δ 1.30–2.20 (m, 12H), 2.27–2.37 (m, 6H), 2.50 –2.60 (m, 1H), 3.30–3.80 (m, 5H), 3.55 (s, 2H), 3.66–3.73 (m, 6H), 4.10–4.20 (m, 1H), 6.60–7.55 (m, 7H), 8.03 (m, 1H), 8.15 (m, 1H).

Provenance & Evidence