Ammonium formate → HCID 85850735, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3 g (10 mmol) of (R/S)-1-benzyl-pyrrolidin-3-ylphosphonic acid, diethyl ester (from Step A), 9.5 g (150 mmol) of ammonium formate and 1.0 g of 10% palladium on charcoal in 60 mL of MeOH was warmed to 40° C. for 1.5 h. The reaction was cooled, filtered through a pad of celite and concentrated. The mixture was partitioned between 75 mL of 1N NaOH and 100 mL of CH2Cl2. After separating layers, the aqueous phase was extracted with 3×100 mL of CH2Cl2. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified on a 40M Biotage column using 90:10:1 v/v/v CH2Cl2/MeOH/NH4OH as the eluant to afford the title compound as a pale yellow oil: RF: 0.13 (95:5:0.5 v/v/v CH2Cl2MeOH/NH4OH); 1H-NMR (500 MHz) δ 1.22 (t, J=7.1, 6H), 1.81 (m, 1H), 1.95 (m, 1H), 2.25 (m, 1H), 2.73 (m, 1H), 2.89-2.99 (m, 3H), 4.06-4.16 (m, 4H).

Provenance & Evidence