methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate → tert-butyl N-[(3S)-2-oxooxolan-3-yl]carbamate

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Reaction Steps

A mixture of N-tert-butoxycarbonyl-O-benzyl-L-homoserine methyl ester (A, 3.13 g) and 10% palladium on activated carbon (0.93 g) in methanol (160 mL) was stirred at room temperature for 14.5 hr under hydrogen. The catalysts were removed by filtration and washed with methanol. The combined organic layers were evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol=40:1 to 20:1, v/v) to afford the title compound (1.65 g) as a white powder: 1H NMR (400 MHz, CDCl3) δ 1.4-1.5 (m, 9H), 2.20 (m, 1H), 2.77 (m, 1H), 4.25 (m, 1H), 4.35 (m, 1H), 4.45 (t, J=8.8 Hz, 1H), 5.07 (m, 1H).

Provenance & Evidence