Tetrabutylammonium Fluoride → HCID 69015560, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve tert-butyl 5-bromo-3(R)-formyl-8-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (400.0 mg, 0.001080 mol) and 1-(3,5-difluorophenyl)-2-nitroethane (305 mg, 0.00162) in tetrahydrofuran (3.00 mL) and cool to 0° C. celsius. Add 1.00 M tetra-n-butylammonium fluoride in tetrahydrofuran (1.48 mL) and stir at 0° C. for 40 minutes. Dilute the reaction mixture with ethyl acetate (75 mL), water (20 mL) and saturated aqueous sodium chloride (5 mL). Shake well and separate the layers. Wash the organic layer with water (2×25 mL), saturated aqueous sodium chloride (1×25 mL) and dry over magnesium sulfate. Purify (Biotage medium pressure chromatography eluting with 10% ethyl acetate:hexanes) to give the desired product (234 mg, 37%) as a white solid.

Provenance & Evidence