Water → (R)-(+)-1-Boc-3-aminopyrrolidine

Participants

Reaction Steps

tert-Butyl-(3R)-3-[(trifluoroacetyl)amino]pyrrolidine-1-carboxylate 6-1 (6.30 g, 22.32 mmol) was dissolved in 80 mL of 4:1 THF: H2O. Lithium hydroxide hydrate (1.873 g, 44.64 mmol) was added and the reaction was stirred at room temperature. After 24 hours more lithium hydroxide hydrate (2.810 g, 66.96 mmol) was added. After 30 hours the solution was concentrated in vacuo (to remove THE) then extracted with EtOAc (3×). The combined organic layers were dried (Na2SO4), filtered, and concentrated to afford tert-butyl (3R)-3-aminopyrrolidine-1-carboxylate 6-2 as a yellow oil. Free base: 1H NMR (DMSO-d6) δ 3.45-3.14 (m, 4H), 2.88-2.83 (m, 1H), 1.92-1.77 (m, 1H), 1.61 (s, 2H), 1.56-1.46 (m, 1H), 1.39 (s, 9H).

Provenance & Evidence