Sodium Hydroxide → HCID 23653901, compound

Participants

Reaction Steps

150 mg of 12 (258 μmol) in 1.4 ml of THF and 2.78 ml of 1N hydrochloric acid are introduced into a 25 ml round-bottomed flask, with agitation and under argon. The agitation is maintained for 4.5 h at AT. The medium is neutralized with NaOH (1N), to pH 7, and extracted with 2 times 3 ml of EtOAc. The combined organic phases are dried over MgSO4, filtered and evaporated to dryness. The crude is chromatographed on a silica cartridge (10 g), elution being carried out with CH2Cl2/MeOH (as an MeOH gradient of 1 to 10%). 65 mg of expected product Ex3 are recovered. 40 mg of Ex3 are separated by preparative chiral HPLC (Chirapad AD-H 5 μm 250×4.6 mm, flow rate 1 ml/min, mobile phase: 50% heptane-50% EtOH, 0.1% TEA), to give 9 mg of Ex3a (tr=7.48 min) and 20 mg of Ex3b (tr=9.71 min).

Provenance & Evidence