Triphenylphosphine → Methyl 3-(3-{[(benzyloxy)carbonyl]amino}propoxy)benzoate

Participants

Reaction Steps

A mixture of methyl 3-hydroxybenzoate (609 mg, 4 mmol), benzyl N-(3-hydroxypropyl)carbamate (754 mg, 3.6 mmol) and polymer supported triphenylphosphine (PS—PPh3) (4 g, 12 mmol) in THF (40 mL) was stirred and diethyl azodicarboxylate (948 mg, 5.44 mmol) was added as a solution in THF (4 mL). The mixture was stirred for 16 h then was filtered and washed with DCM and concentrated by evaporation. The residue was purified by chromatography eluting with DCM to give the title compound (481 mg, 35%) as an oil; 1H NMR δ 1.85-1.92 (2H, m), 3.19 (2H, q), 3.86 (3H, s), 4.05 (2H, t), 5.02 (2H, s), 7.20-7.22 (1H, m), 7.29-7.38 (5H, m), 7.42-7.45 (2H, m), 7.53-7.56 (1H, m).

Provenance & Evidence