Methylparaben → HCID 20737849, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of N-Boc-2-(S)-hydroxymethyl-5-(R)-methylpyrrolidine (820 mg, 3.81 mmol), triphenylphosphine (1.10 g, 4.19 mmol) and methyl 4-hydroxybenzoate (580 mg, 3.81 mmol) was added diisopropyl azodicarboxylate (841 ml, 4.19 mmol) at rt, and the resulting mixture was stirred at 60° C. for 1 h. The mixture was concentrated in vacuo, and the residue was chromatographed on silica gel with hexane-EtOAc (5:1) as eluent to give methyl 4-[N-Boc-5-(R)-methyl-2-(S)-pyrrolidinylmethoxy]benzoate (1.32 g, 80%) as a colorless oil. 1H-NMR (CDCl3) δ1.24 (brs, 3 H), 1.49 (s, 9 H), 1.55-1.70 (m, 2 H), 1.94-2.11 (m, 2 H), 3.88 (s, 3 H), 3.88 (overlap, 1H), 4.06-4.20 (m, 2H), 6.93-6.96 (m, 2H), 7.97 (d, J=8.8 Hz, 2 H); MS (ESI) m/z, 350 (M++H).

Provenance & Evidence