Bis(2-methoxyethyl)(4-nitro-3-methoxybenzyl)phosphonate → Bis(2-methoxyethyl)(4-amino-3-methoxybenzyl)phosphonate

Participants

Reaction Steps

A mixture of bis(2-methoxyethyl)(4-nitro-3-methoxybenzyl)phosphonate (Compound 217D, 4.5 g, 12.4 mmol) and 5% Pd/C (2 g, wet) in MeOH (100 mL) was hydrogenated under 50 psi hydrogen pressure at 50° C. for 18 h. The reaction mixture was filtered and the filtrate was concentrated to give the desired product (4 g, 97%). 1H NMR (DMSO-d6, 400 MHz): δ=3.11 (d, J=21.2 Hz, 2H), 3.34 (s, 6H), 3.49 (m, 4H), 3.81 (s, 3H), 4.05 (m, 4H), 6.12 (d, J=8.4 Hz, 2H), 6.20 (dd, J=8.4 Hz, 1H), 6.78 (s, 1H).

Provenance & Evidence