Triacetoxyperiodinane → Benzyl N-methyl-N-(2-oxoethyl)carbamate

Participants

Reaction Steps

A solution of phenylmethyl (2-hydroxyethyl)methylcarbamate (2.02 g, 9.64 mmol) and Dess Martin's Reagent (6.36 g, 15.6 mmol) in CH2Cl2 (100 mL) were combined under nitrogen and stirred for 4 h at ambient temperature. Added CH2Cl2 (100 mL) and washed the organics with 2M Na2CO3 (aq.), saturated NaHCO3, water, and brine, dried over Na2SO4, filtered and evaporated in vacuo. Purified the residue by flash chromatography using silica gel and a gradient between 0 and 10% MeOH in CH2Cl2 over 20 minutes to provide the desired material, after combining and concentrating pure fractions in vacuo, as a yellow viscous oil: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 3.03 (d, J=6.59 Hz, 3 H), 4.06 (s, 1 H), 4.13 (s, 1 H), 5.12-5.21 (m, 2 H), 7.29-7.40 (m, 5 H), 9.63 (d, J=16.28 Hz, 1 H); ES+ MS: 230 (M+Na+).

Provenance & Evidence