Ozone → N-(3-Hydroxy-1-phenylpropyl)-N-methylbenzenesulfonamide

Participants

Reaction Steps

Ozone was bubbled through a solution of the product of Step 1 (1.0 g, 3.3 mmol) in MeOH (50 mL) at −78° C. for 30 min, then after appearance of a pale blue colour, the reaction was purged with N2 for several minutes and NaBH4 (245 mg, 6.6 mmol) was added. The resulting solution was allowed to warm to RT and stirred for a further 15 min at RT. The reaction was quenched by the addition of NH4Cl solution (10 mL) and then concentrated under reduced pressure. H2O (50 mL) was added and then extracted with EtOAc (100 ml and 50 mL). The combined organic extracts were dried (MgSO4) and then concentrated under reduced pressure to yield the alcohol (0.94 g, 93%). 1H NMR (CDCl3, 400 MHz) δ 7.81 (2H, d, J=7.2 Hz), 7.65–7.45 (3H, m), 7.20–7.13 (3H, m), 6.93 (2H, d, J=7.5 Hz), 5.25 (1H, dd, J=9.1, 6.3 Hz), 3.90–3.80 (1H, m), 3.74–3.59 (1H, m), 2.63 (3H, s), 2.13–1.98 (2H, m).

Provenance & Evidence