Lithium borohydride → HCID 69024598, compound

Participants

Reaction Steps

To a solution of methyl N-[(benzyloxy)carbonyl]-O-methyl-L-serinate (60 g, 0.22 mol) in methanol (600 mL) was added lithium borohydride (39.2 g, 1.80 mol). After 2 hours, the reaction mixture was quenched with saturated aqueous ammonium chloride solution, partially concentrated under reduced pressure, and diluted with water. The mixture was extracted with ethyl acetate (3×100 mL), and the combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified via chromatography on silica gel to give benzyl [(2R)-1-hydroxy-3-methoxypropan-2-yl]carbamate. MS ESI calc'd. for C12H18NO4 [M+H]+ 240. found 240. 1H NMR (400 MHz, CDCl3) δ 7.56-7.30 (m, 5H), 5.52 (br s, 1H), 5.08 (s, 2H), 3.84 (d, J=16.0 Hz, 2H), 3.76-3.64 (m, 1H), 3.63-3.52 (m, 2H), 3.38 (s, 3H), 2.55 (bs, 1H).

Provenance & Evidence