Dimethylformamide → HCID 20792949, compound

Participants

Reaction Conditions

Reaction Steps

To N-Boc-(2S,3S)-3-hydroxypyrrolidine-2-carboxylic acid (1.36 g) in DMF (6 ml) added ammonium bicarbonate (0.5 g) and dicyclohexylcarbodiimide (1.3 g). After stirring at 20° C. for 20 h the reaction was concentrated by evaporation under reduced pressure, and the residue triturated with ethyl acetate. The soluble material was purified by chromatography on silica eluting with 50-100% (5% acetic acid in diethyl ether) in hexane to give the title material as a colourless gum, (0.5 g). NMR (CD3OD) major rotamer: 1.43, (s, 9H), 1.88 (m, 1H), 2.0 (m, 1H), 3.55 (m, 2H), 4.03(s, 1H), 4.31 (bs, 1H); minor rotamer: 1.47, (s, 9H), 1.7 (m, 1H), 2.0 (m, 1H), 3.55 (m, 2H), 4.09(s, 1H), 4.34 (d, J=4 Hz, 1H).

Provenance & Evidence