(R)-tert-Butyl 1-azido-3-methoxypropan-2-ylcarbamate → tert-butyl N-((2R)-1-amino-3-methoxypropan-2-yl)carbamate

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A mixture of (R)-tert-butyl 1-azido-3-methoxypropan-2-ylcarbamate (4.3 g, 18.7 mmol) and 10% Pd/C (1.5 g) in MeOH was stirred at RT under H2 atmosphere overnight. After filtration, the crude product was purified by amino-protected silica gel chromatography eluting with EtOAc and petroleum ether (EtOAc/PE=1/1) to give the title compound (740 mg, 19.4%). 1H NMR (400 MHz, CD3OD) δ ppm 5.00 (s, 1 H), 3.67-3.66 (m, 1 H), 3.51-3.47 (m, 1H), 3.42-3.38 (m, 1 H), 3.35 (s, 1 H), 2.82-2.78 (m, 2 H), 1.46 (s, 9 H). [M+H] calc'd for C9H20N2O3, 205; found, 205.

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