benzyl (3R,4R)-3-((tert-butoxycarbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate → (4-Hydroxy-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

A racemic mixture of trans-benzyl 3-(tert-butoxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (3.36 g, 9.99 mmol) (Method 190) in MeOH (40 mL) was degassed, then 10 wt % Pd/C (3.19 g, 3.00 mmol) was added. The mixture was degassed, charged with H2, and stirred overnight. The mixture was filtered through a bed of Celite, washed with methanol, the filtrate was dried over anhydrous Na2SO4, filtered and conc. in vacuo to yield a white solid as racemic tert-butyl-4-hydroxypyrrolidin-3-ylcarbamate (2.020 g, 100%). 1 H NMR (400 MHz, MeOD) δ ppm 4.13 (dt, 1 H), 3.89-3.75 (m, 1 H), 3.35 (brs, 1 H), 3.14 (dd, 1 H), 2.93-2.73 (m, 2 H), 1.46 (s, 10 H); m/z 203.

Provenance & Evidence