Acetic Acid → HCID 58392737, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of intermediate 118 (629 mg; 1.28 mmol) in methanol (13 ml; 0.1 M), NaCNBH3 (169 mg; 2.56 mmol) is added at 0° C.; pH is adjusted to 5 by addition of acetic acid. The reaction mixture is stirred at 0° C. for 2 hours and at RT for 5 hours, then it is poured into brine (50 ml), and pH is adjusted to 7 by addition of a saturated solution of NaHCO3. The aqueous phase is extracted with AcOEt (3×60 ml) and the combined organic layers are concentrated. The crude material is purified by silica gel flash chromatography in gradient elution from DCM to DCM/MeOH 88:12, to afford pure title compound (335 mg, 53% yield mixture of stereoisomers).

Provenance & Evidence