Triacetoxyperiodinane → HCID 59396019, compound

Participants

Reaction Steps

To a solution of phenylmethyl (1S,4S,6S)-4-(hydroxymethyl)-3-azabicyclo[4.1.0]heptane-3-carboxylate D9 (0.447 g) in DCM (13 ml) was added NaHCO3 (0.575 g, 6.84 mmol) and Dess-Martin periodinane (0.798 g, 1.882 mmol) and stirred at room temperature. TLC (Cyclohexane/EtOAc 1/1,2,4-dinitrophenylidrazine) showed the absence of starting material, so a solution of saturated NaHCO3/5% Na2S2O3 (60 ml) and DCM (10 ml) were added to the reaction mixture and it was left stirring for 30 minutes. The aqueous phase was back extracted with DCM (3×10 mls) and the biphasic system was passed through a phase separator cartridge. The organic solvent was evaporated under reduced pressure to yield a yellowish oil purified via Biotage SP4 (silica gel, SNAP 25 g; Cy/EtOAc, 25 CV from 1/0 to 7/3). Collected fractions gave the title compound D10 (0.370 g). MS: (ES/+) m/z: 260 (M+1), C15H17NO3 requires 259. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.50-9.38 (m, 1 H), 7.48-7.18 (m, 5 H), 5.19-4.93 (m, 2 H), 4.31-3.83 (m, 2 H), 3.28-2.90 (m, 1 H), 2.30-2.15 (m, 1H), 1.77-1.30 (m, 1 H), 1.21-0.84 (m, 2 H), 0.56-0.75 (m, 1 H), 0.22-0.03 (m, 1 H).

Provenance & Evidence