Lithium hydroxide, monohydrate → HCID 58865564, compound

Participants

Reaction Steps

To a stirred solution of 327 (16.0 mmol) in 1,4-dioxane (120 mL) was added LiOH.H2O (32.0 mmol, 2 equiv). The suspension was allowed to stir at room temperature for 16 h at which point TLC indicated complete consumption of starting material (KMnO4 stain for S.M.). The reaction was diluted with THF (120 mL), filtered through a glass frit and concentrated. The resulting syrup was diluted with THF/CHCl3 (1:1, 200 mL) and washed with saturated NaHCO3 (100 mL), brine (100 mL), dried (MgSO4), and purified via column chromatography (0–10% MeOH in CH2Cl2 with 0–1% NH4OH) to give [5-(S)-(tert-Butoxycarbonylamino-methyl)-pyrrolidin-3-(S)-yl]-carbamic acid tert-butyl ester (328) as a colorless foam. 1H NMR (400 MHz, CD3OD) δ=1.45 ppm (s, 9H), 1.47 (s, 9H), 1.69 (br s, 1H), 2.32–2.39 (m, 1H), 2.82 (dd, 1H, J=6, 13 Hz), 2.89 (dd, 1H, J=4, 13 Hz), 3.00 (dd, 1H, J=7, 11 Hz), 3.81 (dd, 1H, J=7, 11 Hz), 3.92–3.98 (m, 1H); 13C NMR (100 MHz, DMSO-d6) δ=26.0, 29.0, 29.1, 58.9, 67.8, 78.5, 79.1, 154.3, 155.7 pm.

Provenance & Evidence