Methyl morpholine oxide → HCID 21864738, compound

Participants

Reaction Steps

6-Fluoro-1,4-dihydro-1,4-methano-naphthalene (680 mg, 4.22 mmol) and N-methyl morpholine N-oxide (599 mg, 4 43 mmol) were stirred in acetone (50 mL) and H2O (5 mL). To this was added a solution of OsO4 (0.2 mL. 2.5% wt solution in t-BuOH, 0.02 mmol) After 72 hours, flonsil (5 g) and saturated aqueous NaHSO3 solution (3 mL) were added and stirred for 1 hour. The flonsil was filtered and the filtrate concentrated to produce a crystalline product which was triturated with acetone and filtered (524 mg, 64%). 1H NMR (400 MHz, CDCl3) δ 7.10 (dd, J=8.0, 5.0 Hz, 1H), 6 90 (dd, J=8 0, 2.3 Hz, 1H), 6 75 (ddd, J=8 0, 8.0, 2.3 Hz, 1H), 3.79 (s, 2H), 3.18 (d, J=1 5 Hz, 2H), 2.22 (d, J=10 0 Hz, 1H), 1 92 (dd, J=10 0, 1.5 Hz, 1H) GCMS m/e 194 (M+)

Provenance & Evidence