Aniline → (3R*,4R*)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-phenylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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A solution of (3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (100 mg, 0.20 mmol) and aniline (26 μL, 0.28 mmol) in 1,2-dichloroethane (5 mL) is stirred 25 min, before the addition of NaBH(OAc)3 (60 mg, 0.28 mmol) follows. The solution is stirred overnight at RT, then diluted with CH2Cl2 and washed with an aqueous saturated solution of NaHCO3. The combined organic extracts are dried over Na2SO4 and concentrated. The crude material is purified by flash chromatography on silica gel (eluent: CH2Cl2/MeOH 100:0 to 97:3) to give the title product. TLC, Rf (CH2Cl2/MeOH 95:5)=0.25. MS (LC-MS): 570.0 [M+H]+; tR (HPLC, nucleosil C18 column, 10-100% CH3CN/H2O/ 5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 5.31 min.

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