Water → HCID 58111002, compound

Participants

Reaction Steps

To a stirred solution of benzyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutylcarbamate (Step 2, 1.3 g, 4.72 mmol) in dioxane (90 ml): water (30 ml) aq. NaOBr solution (80 ml) was added slowly at about −5° C. and stirred at the same temperature for about 5 hours. After completion of the reaction (monitored by TLC), the reaction mixture was washed with methyl t-butyl ether and the aqueous layer was adjusted pH (2-3) with 1N HCl and extracted with EtOAc, dried over Na2SO4 and the solvent was evaporated then the resulting crude was purified by silica gel column (100-200 mesh, elution: 20% EtOAc in Hexane) to afford the title compound as a semi solid. Wt: 1.2 g: Yield: 92%; 1H NMR (300 MHZ, CDCl3): δ 7.38-7.31 (m, 5H), 5.09 (q, 2H, J=10.8 Hz), 4.89 (d, 1H, J=8.4 Hz), 3.98-3.89 (m, 1H), 2.64-2.53 (m, 1H), 2.51-2.26 (m, 2H), 1.32 (s, 3H), 0.98 (s, 3H). IR (KBr, cm−1): 3411, 3351, 2961, 1705, 1532, 1456, 1412, 1343, 1256, 1044, 1003, 776, 697; Mass: [M+Na]+ 300 (100%).

Provenance & Evidence