Sodium borohydride → Methyl 5-(3-((3R)-3-((E)-3-hydroxy-4-(3-(trifluoromethyl)phenyl)but-1-en-1-yl)-1,1-dioxidoisothiazolidin-2-yl)propyl)thiophene-2-carboxylate

Participants

Reaction Steps

Sodium tetrahydridoborate (22 mg, 0.58 mmol) was added to a solution of the enone 12 (268 mg, 0.52 mmol) in MeOH (3.0 mL) at 0° C. The reaction was gradually allowed to warm to room temperature and stirred an additional 5 h. The solvent was removed in vacuo. The residue was partitioned between EtOAc and saturated aqueous ammonium chloride. The organic portion was separated then washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 3:1 EtOAc/hex) afforded 24 mg (9%) of pure alcohol 13.

Provenance & Evidence