Pyrrolidine → N-((1S,2R,3R,4R,6R)-2,3-bis(benzyloxy)-4-((benzyloxy)methyl)-6-hydroxycyclohexyl)pyrrolidine-1-carbothioamide

Participants

Reaction Steps

A mixture of (1R,2S,3R,4R,5R)-2-amino-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)cyclohexanol (0.210 g, 0.469 mmol), 1,1-thiocarbonyldiimidazole (Thio-CDI) (0.125 g, 0.704 mmol) in DCM (10 mL) was stirred at room temperature for 3 h. Pyrrolidine (0.10 mL) was then added, and the mixture was further stirred for 1 h. The solvent was removed under reduced pressure, and the residue was purified on silica gel by automatic flash column chromatography (EtOAc/hexanes, 2:3 to 4:1), affording the product as a pale yellow solid (0.26 g, 99%). 1H NMR (400 MHz, CDCl3) δ 7.29-7.16 (m, 15H), 5.06 (d, J=7.5 Hz, 1H), 4.77 (d, J=12.0 Hz, 1H), 4.71 (d, J=10.8 Hz, 1H), 4.70-4.66 (m, 1H), 4.57 (d, J=12.0 Hz, 1H), 4.50 (d, J=10.8 Hz, 1H), 4.42 (s, 2H), 4.19 (s, broad, 1H), 3.65 (t, J=8.8 Hz, 1H), 3.56 (dd, J=4.5, 8.8 Hz, 1H), 3.51-3.40 (m, 3H), 2.07-2.02 (m, 1H), 1.76-1.62 (m, 6H).

Provenance & Evidence