(4R)-4-Methyl-2-oxazolidinone

To a mixture of D-alaninol (8.65 g, 0.12 mmol) in toluene and aqueous KOH (124 mL, 12.5percent aq, 0.28 mmol) at 0 °C was added phosgene (72.7 mL, 20percent in toluene, 0.14 mmol) at such a rate that the internal temperature remained < 5 °C. The reaction mixture was stirred at 0 °C for a further 40 minutes then evaporated to dryness. The crude residue was extracted with industrial methylate spirits, the slurry was filtered and the filtrate evaporated in vacuo. The resultant residue was purified via flash chromatography on silica gel (solvent gradient: 40-100percent ethyl acetate in cyclohexane) to yield 10.4 g (90percent) of the title compound as a white solid. H NMR (400 MHz, CDC13) δ 6.00 (br s, 1H), 4.50 (t, J = 6.5 Hz, 1H), 4.07 - 3.97 (m, 1H), 3.95 (dd, J = 7.8, 6.2 Hz, 1H), 1.30 (d, J = 6.1 Hz, 3H).To a mixture of D-alaninol (8.65 g, 0.12 mmol) in toluene and aqueous KOH (124 mL, 12.5percent aq, 0.28 mmol) at 0° C. was added phosgene (72.7 mL, 20percent in toluene, 0.14 mmol) at such a rate that the internal temperature remained <5° C. A solution of triphosgene (0.297 g, 1 .0 mmcl) in DCM (5 mL) was added portion-wise over I hto a solution of (2R)-2-aminopropan-1-ol (0.156 mL, 2.0 mmol) and triethylamine (0.56 mL, 4.0mmol) in DCM (5 mL), precooled in ice-water. The mixture was stirred in ice-water fora further 2 h, then ether (6 mL) was added. The thick suspension was filtered through a sinter, washing the solid with more ether (6 mL). The filtrate was concentrated onto flash silica (5 mL) and the resulting powder was purified by column chromatography (normal phase, [Biotage SNAPcartridge KP-sil 25 g, 40-63 JLm, 60 A], 30 mL per mm, 100percent EtOAc) to give(4R)-4-methyl-1, 3-oxazolidin-2-one (192 mg, 95percent) as a solid.LCMS (Method C): mlz 102 (M+H) (ES’), at 0.14 mm, UV inactive

Molecular Weight:101.10
XLogP3:0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:101.047678466
Monoisotopic Mass:101.047678466
Topological Polar Surface Area:38.3
Heavy Atom Count:7
Complexity:91.7
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes