Acetone → Ammonia

Participants

Reaction Steps

To a solution of 3-(4-allylamino-3,5-dimethyl-phenyl)-1-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (80 mg, 0.195 mmol) and NMO (69 mg, 0.507 mmol) in acetone (11.5 mL) and water (1.65 mL), a 2.5 M solution of OsO4 in tert. butanol (88 μL, 7 μmol) is added. The mixture is stirred at rt for 18 h and then separated by prep. HPLC (Waters Symmetry C18 19×50 mm 5 μm, 10-95% acetonitrile in water containing 0.5% of 25% aq. NH3) to afford 3-[4-(2,3-dihydroxy-propylamino)-3,5-dimethyl-phenyl]-1-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (52 mg) as a pyle yellow solid; LC-MS: tR=0.90 min, [M+1]+=444.41; 1H NMR (CDCl3): δ 6.98 (s, 2H), 3.92-3.84 (m, 1H), 3.80 (dd, J=3.5, 11.1 Hz, 1H), 3.72 (dd, J=4.7, 11.1 Hz, 1H), 3.14-2.88 (m, 7H), 2.72 (q, J=7.6 Hz, 2H), 2.30 (s, 2H), 2.29 (s, 6H), 1.54 (t, J=6.4 Hz, 2H), 1.26 (t, J=7.6 Hz, 3H), 0.96 (s, 6H).

Provenance & Evidence