Water → HCID 53893975, compound

Participants

Reaction Steps

To a solution of nipecotic acid (1.66 g, 12.8 mmol) in 2 N NaOH (12.8 mL, 25.6 mmol) and dioxane (30 mL) was added 1,3-bis(benzyloxycarbonyl)-2-methyl-2-thiopseudourea (4.6 g, 12.8 mmol). After 48 h, the reaction mixture was added to H2O (200 mL) and Et2O (200 mL). The aqueous layer was separated and extracted with Et2O (2×200 mL). The aqueous layer was acidified to pH, 2.0 with 3 N HCl and extracted with EtOAc (500 mL). The organic layer was MgSO4 dried and concentrated to give the title compound (4.0 g, 71%): TLC Rf=0.65 (1:15:135 Acetic Acid:Methanol:Chloroform); NMR (CDCl3) δ1.55-1.92 (m, 6H), 2.00-2.15 (m, 1H), 2.70-2.80 (m, 1H), 3.20-3.35 (q, 1H), 3.38-3.45 (m, 1H), 3.75-4.10 (m, 1H), 5.10 (s, 2H), 5.22 (s, 2H), 7.30-7.40 (m, 10H); FD-MS 440 (NH+).

Provenance & Evidence