Methylparaben → HCID 20737850, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-Boc-2-(S)-hydoxymethyl-5-(R)-phenylpyrrolidine (1.10 g, 3.97 mmol), triphenylphosphine (1.25 g, 4.76 mmol) and methyl 4-hydroxybenzoate (724 mg, 4.76 mmol) was added diisopropyl azodicarboxylate (955 ml, 4.76 mmol) at rt, and the resulting mixture was stirred at 60° C. for 45 min. The mixture was concentrated in vacuo, and the residue was chromatographed on silica gel with hexane-EtOAc (4:1) as eluent to give methyl 4-[N-Boc-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate (1.31 g, 80%) as a colorless oil. 1H-NMR (CDCl3) δ 1.19 and 1.47 (br s, total 9 H), 2.09–2.15 (m, 3 H), 2.33–2.37 (m, 1 H), 3.94 (s, 3 H), 4.30 (br s, 1 H), 4.41 (br s, 2 H), 4.77 (br s, 1 H), 7.03 (d, J=8.8 Hz, 2 H), 7.24–7.36 (m, 5 H), 8.03–8.06 (m, 2 H); MS (ESI) m/z, 412 (M++H).

Provenance & Evidence